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[ CAS No. 6153-39-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 6153-39-5
Chemical Structure| 6153-39-5
Structure of 6153-39-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 6153-39-5 ]

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Product Details of [ 6153-39-5 ]

CAS No. :6153-39-5 MDL No. :MFCD00149092
Formula : C7H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :NBKPNAMTHBIMLA-UHFFFAOYSA-N
M.W : 142.15 Pubchem ID :3083941
Synonyms :

Calculated chemistry of [ 6153-39-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 38.5
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.78
Log Po/w (XLOGP3) : 1.1
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : 0.27
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 0.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.86
Solubility : 1.97 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (Ali) : -1.74
Solubility : 2.61 mg/ml ; 0.0184 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.59
Solubility : 3.65 mg/ml ; 0.0257 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 6153-39-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6153-39-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6153-39-5 ]

[ 6153-39-5 ] Synthesis Path-Downstream   1~93

  • 1
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  • [ 6153-39-5 ]
  • 7-Ethoxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 22
  • [ 6153-39-5 ]
  • 7-Isopropoxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 23
  • [ 6153-39-5 ]
  • 2,2,5-Trimethyl-7-propoxy-chroman-4-ol [ No CAS ]
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  • [ 6153-39-5 ]
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  • [ 121404-52-2 ]
  • 28
  • [ 6153-39-5 ]
  • 2,2,5-Trimethyl-7-prop-2-ynyloxy-chroman-4-ol [ No CAS ]
  • 29
  • [ 6153-39-5 ]
  • 7-Allyloxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 30
  • [ 6153-39-5 ]
  • [ 94244-02-7 ]
  • 32
  • [ 6153-39-5 ]
  • 7-Isobutoxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 33
  • [ 6153-39-5 ]
  • 7-Butoxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 34
  • [ 6153-39-5 ]
  • [ 120623-21-4 ]
  • 35
  • [ 6153-39-5 ]
  • [ 121404-46-4 ]
  • 36
  • [ 6153-39-5 ]
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  • 37
  • [ 6153-39-5 ]
  • [ 121404-47-5 ]
  • 38
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  • [ 121404-48-6 ]
  • 39
  • [ 6153-39-5 ]
  • 7-Cyclopentyloxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 40
  • [ 6153-39-5 ]
  • 2,2,5-Trimethyl-7-(3-methyl-but-2-enyloxy)-chroman-4-ol [ No CAS ]
  • 41
  • [ 6153-39-5 ]
  • 7-Cyclohexyloxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 42
  • [ 6153-39-5 ]
  • [ 121404-55-5 ]
  • 43
  • [ 6153-39-5 ]
  • 7-Cycloheptyloxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 44
  • [ 6153-39-5 ]
  • 7-Benzyloxy-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 45
  • [ 6153-39-5 ]
  • [ 121404-54-4 ]
  • 46
  • [ 6153-39-5 ]
  • [ 121404-50-0 ]
  • 47
  • [ 6153-39-5 ]
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  • 48
  • [ 6153-39-5 ]
  • [ 121404-56-6 ]
  • 49
  • [ 6153-39-5 ]
  • [ 121404-53-3 ]
  • 50
  • [ 6153-39-5 ]
  • [ 882276-94-0 ]
  • 51
  • [ 6153-39-5 ]
  • 7-(2-Chloro-benzyloxy)-2,2,5-trimethyl-chroman-4-ol [ No CAS ]
  • 52
  • [ 6153-39-5 ]
  • 2,2,5-Trimethyl-7-(naphthalen-1-ylmethoxy)-chroman-4-ol [ No CAS ]
  • 53
  • ammonium thiocyanate [ No CAS ]
  • [ 7758-99-8 ]
  • [ 6153-39-5 ]
  • 6-hydroxy-4-methyl-benz[1,3]oxathiol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; water; (i) Preparation of 6-hydroxy-4-methyl-1,3-benzoxathiol-2-one Ammonium thiocyanate (10.71 g, 141 mmol) was added slowly to a solution of 5-methylres<strong>[6153-39-5]orcinol hydrate</strong> (5.0 g, 35 mmol) and copper(II) sulfate (17.56 g, 70 mmol) in water (100 mL), and the solution was stirred for 18 h. Diethyl ether (100 mL) was added and the mixture was filtered through Celite, washing the cake with diethyl ether (100 mL). The diethyl ether layers were separated and the aqueous layer was re-extracted with diethyl ether (100 mL). The combined organic fractions were dried (MgSO4) and evaporated to a yellow-orange solid (5.30 g, 83%). 1H NMR showed the material to be 80-90% pure and this was taken on without further purification; deltaH (d6-DMSO, 400 MHz) 2.30 (3H, s), 6.57 (1H, s), 6.65 (1H, s), 9.90 (1H, brs).
  • 54
  • [ 89265-35-0 ]
  • [ 6153-39-5 ]
  • [ 197960-66-0 ]
YieldReaction ConditionsOperation in experiment
44.8% With sodium hydrogencarbonate; In dichloromethane; water; 9. 3-Hydroxy-5-methylphenyl 2-(methylsulfonyl)benzenesulfonate To a stirred solution of 2-methylsulfonylbenzenesulphonyl chloride (3.63 g, 14.2 mmol) and <strong>[6153-39-5]orcinol monohydrate</strong> (2.02 g, 14.2 mmol) in dichloromethane (50 mL) was added saturated NaHCO3 aqueous solution (30 mL) dropwise in 30 min. After stirred vigorously at room temperature for 3 days, water was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered, and concentrated to half of the volume (~60 mL). Hexanes (30-40 mL) were added to initiate crystallization. After standing overnight, the mixture was filtered, and the solid was rinsed with small amount of diethyl ether and dichloromethane to give the title compound as a pale pink solid (2.18 g, 44.8%). 1H NMR (CDCl3) delta 8.43 (dd, 1H, J=1.3, 7.9 Hz), 8.11 (dd, 1H, J=1.3, 7.9 Hz), 7.87 (td, 1H, J=1.4, 7.7 Hz), 7.73 (td, 1H, J=1.4, 7.7 Hz), 6.58 (s, 1H), 6.55 (s, 1H), 6.51 (s, 1H), 3.45 (s, 3H), 2.21 (s, 3H).
26% In dichloromethane; water; sodium hydrogencarbonate; a 5-Methyl-3-[2-(methylsulfonyl)phenylsulfonyloxy]phenol A mixture of <strong>[6153-39-5]orcinol monohydrate</strong> (1.68 g, 12 mmol) and 2-methylsulfonylbenzenesulfonyl chloride (3.0 g, 11.8 mmol) in saturated NaHCO3 (25 mL) and dichloromethane (25 mL) was stirred vigorously at room temperature for one week. The reaction mixture was diluted with 50 mL of water and extracted into dichloromethane (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was treated with dichloromethane and ether to initiate crystallization. The mixture was filtered to provide 1.05 g (26% yield) of a white solid. 1H-NMR (300 MHz, CDCl3) delta2.22 (s, 3H), 3.45 (s, 3H), 5.20 (s, 1H), 6.51 (t, 1H), 6.54 (s, H), 6.61 (s, 1H), 7.74 (td, 1H, J=7.7, 1.4 Hz), 7.87 (td, 1H, J=7.7, 1.3 Hz), 8.12 (dd, 1H, J=7.8, 0.7 Hz), and 8.44 (dd, 1H, J=7.8, 0.5 Hz).
In dichloromethane; water; sodium hydrogencarbonate; a 5-Methyl-3-[2-(methylsulfonyl)phenylsulfonyloxy]phenol A mixture of <strong>[6153-39-5]orcinol monohydrate</strong> (1.68 g, 12 mmol) and 2-methylsulfonylbenzenesulfonyl chloride (3.0 g, 11.8 mmol) in saturated aqueous NaHCO3 (25 mL) and dichloromethane (25 mL) was stirred vigorously at room temperature for one week. The reaction mixture was diluted with 50 mL of water and extracted into dichloromethane (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was treated with dichloromethane and ether to initiate crystallization. The mixture was filtered to provide 1.05 g of a white solid. 1 H-NMR (300 MHz, CDCl3) delta 2.22 (s, 3H), 3.45 (s, 3H), 5.20 (s, 1H), 6.51 (t, 1H), 6.54 (s, 1H), 6.61 (s, 1H), 7.74 (td, 1H, J=1.4, 7.7 Hz), 7.87 (td, 1H, J=1.3, 7.7 Hz), 8.12 (dd, 1H, J=0.66, 7.8 Hz), and 8.44 (dd, 1H, J 0.52, 7.8 Hz).
  • 55
  • [ 100-39-0 ]
  • [ 6153-39-5 ]
  • [ 36776-44-0 ]
YieldReaction ConditionsOperation in experiment
48% With NaH; In water; N,N-dimethyl-formamide; a 3-Benzyloxy-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (7.10 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to a mixture of NaH (95%, 24 g, 100 mmol) in N,N-dimethylformamide (60 mL) and the mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to the mixture and stirred at room temperature for 2 hours. Water (100 mL) was added slowly to the reaction mixture. The reaction mixture was extracted with ethyl acetate (3*100 mL) and then the organic phase was washed with brine (2*50 mL) and dried over Na2SO4. After the solvent was evaporated, the residue was purified by flash column chromatography (silica gel, 3:1 hexane:ethyl acetate) to give the title compound as a yellow oil (5.20 g, 48%). 1H-NMR (300 MHz, CDCl3) delta7.39 (m, 5H), 6.40 (s, 1H), 6.29 (t, J=5.3 Hz, 1H),), 6.26 (s, 1H), 5.25 (s, 1H), 4.99 (s, 2H), 2.26 (s, 3H).
32% With NaH; In water; ethyl acetate; N,N-dimethyl-formamide; a 3-Benzyloxy-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (7.10 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to NaH (2.4 g, 100 mmol) in N,N-dimethylformamide (60 mL). The reaction mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in N,N-dimethylformamide (20 mL) was then added, and the reaction mixture was stirred at ambient temperature for 2 hours. Water (100 mL) was added carefully followed by extraction by ethyl acetate (3*100 mL). The organic phase was washed with brine (2*50 mL), dried over Na2 SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (3:1 hexane/ethyl acetate) to give the title compound as a yellow oil (3.40 g, 32%). 1 H-NMR (300 MHz, CDCl3) delta 7.39 (m, 5 H), 6.40 (s, 1 H), 6.29 (s, 1 H), 6.26 (s, 1 H), 5.00 (s, 2 H), 4.89 (s, 1 H), 2.26 (s, 3 H).
31% With NaH; In water; N,N-dimethyl-formamide; a 3-Benzyloxy-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (7.10 g, 50 mmol) in DMF (20 mL) was added dropwise to NaH (95%, 2.4 g, 100 mmol) in DMF (60 mL). The reaction mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in DMF (20 mL was then added dropwise and the reaction mixture was stirred at room temperature for 2 h. Water (100 mL) was added slowly followed by extraction with ethyl acetate (3*100 mL). The organic phase was washed with brine (2*50 mL), dried over Na2 SO4, and concentrated in vacuo. The residue was then purified by flash column chromatography (3:1 hexane:ethyl acetate) to give the title compound as a yellow oil (3.15 g, 31%). 1H-NMR (300 MHz, CDCl3) 2.26 (s, 3H), 4.99 (s, 2H), 5.25 (s, 1H), 6.26 (s, 1H), 6.29 (t, 1H), 6.40 (s, 1H), 7.39 (m, 5H).
  • 56
  • [ 56542-67-7 ]
  • [ 6153-39-5 ]
  • [ 197960-50-2 ]
YieldReaction ConditionsOperation in experiment
83% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(3-Cyanophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 3-cyanobenzenesulfonyl chloride (2.02 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (2.40 g, 83%). 1 H-NMR (300 MHz, CDCl3) delta 8.12 (s, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.93 (d, J=7.8 Hz, 1H), 7.68 (t, J=7.9 Hz, 1H), 6.56 (s, 1H), 6.36 (s, 1H), 6.30 (s, 1H), 5.35 (s, 1H), 2.22 (s, 3H).
  • 57
  • ethyl acetate-dichloromethane [ No CAS ]
  • [ 701-27-9 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • [ 197960-47-7 ]
YieldReaction ConditionsOperation in experiment
935 mg (68%) In diethyl ether; a 3-(3-Fluorophenylsulfonyloxy)-5-methylphenol To a solution of 0.704 g (5.67 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> and 1.00 g (5.15 mmol) of 3-fluorobenzenesulfonyl chloride in 25 mL of diethyl ether was added 25 mL of saturated aqueous NaHCO3 and the biphasic mixture was stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2*30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2 SO4) and concentrated to 1.41 g of a pale amber-colored oil. This material was flash chromatographed on 65 g of silica gel with 3% ethyl acetate-dichloromethane to afford 935 mg (68%) of the desired product as a colorless syrup: 1 H-NMR (300 MHz; CDCl3) delta 7.66 (ddd, 1H, J=7.8, 1.7, 1.1 Hz), 7.55 (m, 2H), 7.38 (tdd, 1H, J=8.3, 2.6, 1.1 Hz), 6.56 (m, 1H), 6.40 (m, 1H), 6.33 (td, 1H, J=2.2, 0.5 Hz), 5.29 (s, 1H) and 2.23 (s, 3H).
  • 58
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • 5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride [ No CAS ]
  • [ 197960-12-6 ]
YieldReaction ConditionsOperation in experiment
37% In tetrahydrofuran; diethyl ether; a 3-(5-Chloro-1,3-Dimethylpyrazole-4-sulfonyloxy)-5-methylphenol A mixture of <strong>[6153-39-5]orcinol monohydrate</strong> (650 mg, 4.58 mmol) and 1.03 g (4.50 mmol) of 5-chloro-1,3-dimethylpyrazole-4-sulfonyl chloride in diethyl ether (20 mL) and saturated aqueous sodium bicarbonate (20 mL) was stirred overnight. To the reaction mixture was added 15 mL of tetrahydrofuran, and the reaction mixture was heated to 50 C. for 1 h and at 70 C. for 1 h. The reaction mixture was cooled to room temperature, extracted into ethyl acetate, dried (MgSO4), and purified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5 to 93:7)) to give the title compound (558 mg, 37% yield) as an oil. 1 H-NMR (300 MHz, CDCl3) delta 6.91-6.92 (m, 1H), 6.57-6.61 (m, 1H), 6.41-6.50 (m, 1H), 5.93 (s, 1H), 3.82 (s, 3H), 2.29 (s, 3H), 2.25 (s, 3H). Mass spectrum (MALDI-TOF, alpha-cyano-4-hydroxycinnamic acid matrix) calcd. for C12 H13 ClN2 O4 S: 316.9 (M+H). Found: 317.0.
  • 59
  • [ 1483-28-9 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • 3-(2,5-dimethoxyphenylsulfonyloxy)-5-methylphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.29 g (54%) a 3-(2,5-Dimethoxyphenylsulfonyloxy)-5-methylphenol To a solution of 1.00 g (8.05 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> and 1.75 g (7.38 mmol) of 2,5-dimethoxybenzenesulfonyl chloride in 20 mL of diethyf ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2*30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2 SO4) and concentrated to give an amber-colored solid. Recrystallization from ethyl acetate-hexane afforded 1.29 g (54%) of the title compound as a cream-colored powder: 1 H-NMR (300 MHz; CDCl3) delta 7.34 (d, 1 H, J=3.1 Hz), 7.15 (dd, 1 H, J=9.1, 3.1 Hz), 7.02 (d, 1 H, J=9.1 Hz), 6.53 (m, 2 H), 6.42 (t, 1H, J=2.2 Hz), 5.08 (br s, 1 H),3.95 (s,3 H), 3.76 (s, 3 H), and 2.23 (s, 3 H).
  • 60
  • [ 23095-05-8 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • [ 197959-80-1 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; a 3-(5-Bromo-2-methoxyphenylsulfonyloxy)-5-methylphenol To a solution of 1.25 g (8.76 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> and 2.50 g (8.76 mmol) of 5-bromo-2-methoxybenzenesulfonyl chloride in 25 mL of diethyl ether was added 25 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2*30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2 SO4) and concentrated to 1.92 g (59%) of the desired product as a pale yellow crystalline solid: 1 H-NMR (300 MHz; CDCl3) delta 7.93 (d, 1 H, J=2.5 Hz), 7.69 (dd, 1 H, J=8.9, 2.5 Hz), 6.98 (d, 1 H, J=8.9 Hz), 6.54 (br s, 1 H), 6.51 (br s, 1 H), 6.41 (t, 1 H, J=2.2 Hz), 3.98 (s, 3 H) and 2.24 (s, 3 H).
  • 61
  • ethyl acetate-dichloromethane [ No CAS ]
  • [ 2905-24-0 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • [ 197960-53-5 ]
YieldReaction ConditionsOperation in experiment
870 mg (65%) In diethyl ether; a 3-(3-Bromophenylsulfonyloxy)-5-methylphenol To a solution of 534 mg (4.30 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> and 1.00 g (3.91 mmol) of 3-bromobenzenesulfonyl chloride in 25 mL of diethyl ether was added 25 mL of saturated aqueous NaHCO3 and the biphasic mixture was stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2*30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2 SO4) and concentrated to 1.4 g of an amber-colored resin. Chromatography on 65 g of silica gel with 3% ethyl acetate-dichloromethane afforded 870 mg (65%) of the desired product as a colorless syrup: 1 H-NMR (300 MHz; CDCl3) delta 8.02 (t, 1H, J=1.8 Hz), 7.79 (m, 2H), 7.41 (t, 1H, J=7.9 Hz), 6.57 (m, 1H), 6.40 (m, 1H), 6.33 (t, 1H, J=2.2 Hz) and 2.24 (s, 3H).
  • 62
  • [ 445-05-6 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • [ 197960-22-8 ]
YieldReaction ConditionsOperation in experiment
1.24 g (54%) In diethyl ether; a 3-(5-Fluoro-2-methylphenylsulfonyloxy)-5-methylphenol To a solution of 1.00 g (8.05 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> and 1.63 g (7.38 mmol) of 5-fluoro-2-methylbenzenesulfonyl chloride in 20 mL of diethyl ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2*30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2 SO4) and concentrated to give 2.2 g of an orange syrup. Crystallization from dichloromethane-hexane (two crops) afforded 1.24 g (54%) of the title compound as a light orange powder: 1 H-NMR (300 MHz; CDCl3) delta 7.57 (dd, 1H, J=8.2, 2.8 Hz), 7.36 (dd, 1H, J=8.6, 5.2 Hz), 7.22 (td, 1H, J=8.4, 2.8 Hz), 6.52 (m, 1H), 6.39 (m, 1H), 6.30 (t, 1H, J=2.2 Hz), 2.69 (s, 3H) and 2.21 (s, 3H).
  • 63
  • [ 22952-32-5 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • [ 197959-76-5 ]
YieldReaction ConditionsOperation in experiment
86% In tetrahydrofuran; dichloromethane; a 3-(5-Chloro-2-methoxyphenylsulfonyloxy)-5-methylphenol Saturated aqueous NaHCO3 (70 mL) was added to a solution of <strong>[22952-32-5]5-chloro-2-methoxybenzenesulfonyl chloride</strong> (3.83 g, 15.9 mmol) and orcinol monohydrate (3.39 g, 23.9 mmol) in di-n-butyl ether (53 mL) and tetrahydrofuran (17 mL). The biphasic solution was mixed vigorously at 50 C. for 7 h and then at ambient temperature overnight. The reaction mixture was combined with that from a previous reaction (which used 4.53 g ?18.8 mmol! of <strong>[22952-32-5]5-chloro-2-methoxybenzenesulfonyl chloride</strong>), the layers were separated, and the aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic extracts were washed with brine (250 mL), dried over Na2 SO4, filtered, and evaporated to give 18.25 g of a clear brown oil. The product was purified by flash column chromatography (1% to 4% ethyl acetete in dichloromethane) to give the title compound (9.86 g, 86%) as a pale yellow oil which crystallized upon standing. 1 H-NMR (300 MHz, CDCl3) delta 7.81 (d, 1 H, J =2.6 Hz), 7.55 (dd, 1 H, J=2.6, 8.9 Hz), 7.02 (d, 1 H, J=8.9 Hz), 6.53 (m, 2H), 6.41 (t, 1 H, J=2.2 Hz), 3.99 (s, 3 H), 2.24 (s, 3 H). Mass spectrum (MALDI-TOF, alpha-cyano-4-hydroxycinnamic acid matrix) calcd. for C14 H13 ClO5 S: 351.0 (M+Na). Found: 351.1.
  • 64
  • [ 858842-21-4 ]
  • [ 144-55-8 ]
  • [ 6153-39-5 ]
  • [ 197959-95-8 ]
YieldReaction ConditionsOperation in experiment
1.24 g (54%) In diethyl ether; a 3-(2-Methoxy-5-methylphenylsulfonyloxy)-5-methylphenol To a solution of 1.00 g (8.05 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> and 1.63 g (7.38 mmol) of 2-methoxy-m-toluenesulfonyl chloride in 20 mL of diethyl ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2*30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2 SO4) and concentrated to give 2.2 g of an orange syrup. Crystallization from dichloromethane-hexane (two crops) afforded 1.24 g (54%) of the title compound as a light orange powder: 1 H-NMR (300 MHz; CDCl3) delta 7.62 (d, 1 H, J=2.0 Hz), 7.40 (m, 1 H), 6.96 (d, 1 H, J=8.5 Hz), 6.52 (m, 2 H), 6.42 (t, 1 H, J=2.1 Hz), 5.13 (s, 1 H), 3.96 (s, 3 H), 2.29 (s, 3 H) and 2.23 (s, 3 H).
  • 65
  • [ 69360-26-5 ]
  • [ 6153-39-5 ]
  • [ 197959-92-5 ]
YieldReaction ConditionsOperation in experiment
57% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(2-Cyanophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 2-cyanobenzenesulfonyl chloride (2.02 g, 10.0 mmol) were rnixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.65 g, 57%). 1 H-NMR (300 MHz, CDCl3) delta 8.07 (m, 1H), 7.94 (m, 1H), 7.75-7.80 (m, 2H), 6.57 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 5.69 (br s, 1H), 2.22 (s, 3H).
57% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(2-Cyanophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 2-cyanobenzenesulfonyl chloride 2.02 g, 10.0 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether 30 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.65 g, 57%). 1H-NMR (300 MHz, CDCl3) delta8.07 (m, 1H), 7.94 (m, 1H), 7.75-7.80 (m, 2H), 6.57 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 5,69 (br s, 1H), 2.22 (s, 3H).
  • 66
  • [ 776-04-5 ]
  • [ 6153-39-5 ]
  • [ 197959-54-9 ]
YieldReaction ConditionsOperation in experiment
55% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenol <strong>[6153-39-5]Orcinol monohydrate</strong> (2.84 g, 20.0 mmol) and 2-trifluoromethylbenzenesulfonyl chloride (4.90 g, 20.0 mmol) were mixed in saturated aqueous NaHCO3 (70 mL) and diethyl ether (70 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (100 mL) and extracted into ethyl acetate (3*80 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a white solid (3.65 g, 55%). 1 H-NMR (300 MHz, CDCl3) delta 8.12 (d, J=8.0 Hz, 1 H), 7.98 (d, J=7.9 Hz, 1 H), 7.80 (t, J=8.2 Hz, 1 H), 7.69 (t, J=7.8 Hz, 1 H), 6.55 (s, 1 H), 6.48 (s, 1 H), 6.39 (s, 1 H), 5.11 (s, 1 H), 2.23 (s, 3 H).
55% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenol <strong>[6153-39-5]Orcinol monohydrate</strong> (2.84 g. 20.0 mmol) and 2-trifluoromethylbenzenesulfonyl chloride (4.90 g, 20.0 mmol) were mixed in saturated NaHCO3 (70 mL) and diethyl ether (70 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was quenched with water (100 mL) and extracted into ethyl acetate (3*80 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a white solid (3.65 g, 55%). 1H-NMR (300 MHz, CDCl3) delta8.12 (d, J=8.0 Hz, 1H), 7.98 (d, J=7.9 Hz, 1H), 7.80 (t, J=8.2 Hz, 1H), 7.69 (t, J=7.8 Hz, 1H), 6.55 (s, 1H), 6.48 (s, 1H), 6.39 (s, 1H), 5.11 (s, 1H), 2.23 (s, 3H).
  • 67
  • [ 6153-39-5 ]
  • [ 1694-92-4 ]
  • [ 197960-56-8 ]
YieldReaction ConditionsOperation in experiment
73% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 5-Methyl-3-(2-nitrophenylsulfonyloxy)phenol <strong>[6153-39-5]Orcinol monohydrate</strong> (4.27 g, 30.0 mmol) and 2-nitrobenzenesulfonyl chloride (6.65 g, 30.0 mmol) were mixed in saturated aqueous NaHCO3 (100 mL) and diethyl ether (100 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (150 mL) and extracted into ethyl acetate (3*100 mL). The organic phase was washed with brine (2*100 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a pale yellow solid (6.10 g, 73%). 1 H-NMR (300 MHz, CDCl3) delta 8.09 (d, J=7.8 Hz, 1H), 7.85 (m, 2H), 7.71 (m, 1H), 6.62 (s, 1H), 6.59 (s, 1H), 6.51 (s, 1H), 5.06 (s, 1H), 2.26 (s, 3H).
  • 68
  • [ 5402-73-3 ]
  • [ 6153-39-5 ]
  • [ 197959-73-2 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(2,5-Dichlorophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 2,5-dichlorobenzenesulfonyl chloride (2.46 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as apale yellow solid (1.65 g, 51%). 1 H-NMR (300 MHz, CDCl3) delta 7.95 (s, 1H), 7.55 (s, 2H), 6.56 (s, 2H), 6.46 (s, 1H), 5.29 (s, 1H), 2.25 (s, 3H).
  • 69
  • [ 6153-39-5 ]
  • [ 2905-23-9 ]
  • [ 189339-69-3 ]
YieldReaction ConditionsOperation in experiment
71% In diethyl ether; dichloromethane; water; sodium hydrogencarbonate; ethyl acetate; a 3-(2-Chlorophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10 mmol) and 2-chlorobenzenesulfonyl chloride (2.43 g, 11 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature for 2 days. The reaction mixture was diluted with 50 mL of water and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane) to give the title compound as a pale yellow liquid (2.15 g, 71%). 1 H-NMR (300 MHz, CDCl3) delta 2.22 (s, 3 H), 5.24 (s, 1 H), 6.43 (s, 1 H), 6.52 (s, 2H), 7.38 (m, 1 H), 7.60 (m, 2 H), and 7.96 (dd, 1 H, J =0.6, 3.9 Hz).
71% In diethyl ether; dichloromethane; water; sodium hydrogencarbonate; ethyl acetate; c 2-Chlorobenzenesulfonic acid 3-hydroxy-5-methylphenyl ester <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10 mmol) and 2-chlorobenzenesulfonyl chloride (2.43 g, 11 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature for 2 days. The reaction mixture was quenched with 50 mL of water and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (2% ethyl acetate in methylene chloride) to give the title compound as a pale-yellow liquid (2.15 g, 71%). 1 H-NMR (300 MHz, CDCl3) delta 2.22 (s, 3H), 5.24 (s, 1H), 6.43 (s, 1H), 6.52 (s, 2H), 7.38 (m, 1H), 7.60 (m, 2H), and 7.96 (dd, 1H, J=0.6, 3.9 Hz).
  • 70
  • [ 2888-06-4 ]
  • [ 6153-39-5 ]
  • [ 189340-77-0 ]
YieldReaction ConditionsOperation in experiment
69% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(3-Chlorophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 3-chlorobenzenesulfonyl chloride (2.21 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (2.08 g, 69%). 1 H-NMR (300 MHz, CDCl3) delta 7.86 (s, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 6.57 (s, 1H), 6.40 (s, 1H), 6.33 (s, 1H), 5.32 (s, 1H), 2.24 (s, 3H).
69% In diethyl ether; dichloromethane; water; sodium hydrogencarbonate; ethyl acetate; a 3-Chlorobenzenesulfonic acid 3-hydroxy-5-methylphenyl ester 5 <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10 mmol) and 3-chlorobenzenesulfonyl chloride (2.43 g, 11 mmol) were mixed in saturated NaHCO3 (30 mmL and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature for 2 days. After adding water (50 mL) to the mixture, the mixture was extracted with ethyl acetate (3*50 mL). The organic phase was then washed with brine (2*50 mL) and dried over Na2 SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (2% ethyl acetate in methylene chloride) to give the title compound as a pale-yellow liquid (2.08 g, 69%). 1 H-NMR (300 MHz, CDCl3) delta 2.24 (s, 3H), 5.32 (s, 1H), 6.33 (t, 1H, J=2.2 Hz), 6.40 (s, 1H), 6.57 (s, 1H), 7.48 (t, 1H, J=8.0 Hz), 7.65 (m, 1H), 7.73 (m, 1H), and 7.86 (t, 1H, J=1.8 Hz).
  • 71
  • [ 1899-93-0 ]
  • [ 6153-39-5 ]
  • [ 197959-89-0 ]
YieldReaction ConditionsOperation in experiment
76% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 5-Methyl-3-(3-methylphenylsulfonyloxy)phenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 3-methylbenzenesulfonyl chloride (1.60 g, 8.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*40 mL). The organic phase was washed with brine (2*30 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a yellow oil (2.1 g, 76%). 1 H-NMR (300 MHz, CDCl3) delta 7.68 (s, 1H), 7.64 (d, J=7.9 Hz, 1H), 7.45 (t, J=7.8 Hz, 1H), 7.40 (t, J=7.6 Hz, 1H), 6.54 (s, 1H), 6.39 (s, 1H), 6.32 (s, 1H), 5.33 (s, 1H), 2.41 (s, 3H), 2.21 (s, 3H).
  • 72
  • [ 21742-00-7 ]
  • [ 6153-39-5 ]
  • [ 197959-57-2 ]
YieldReaction ConditionsOperation in experiment
41% In ethyl acetate; N,N-dimethyl-formamide; a 5-Methyl-3-(2-trifluoromethylbenzyloxy)phenol <strong>[6153-39-5]Orcinol monohydrate</strong> (4.30 g, 30 mmol) in N,N-dimethylformarnide (20 mL) was added to a suspension of sodium hydride (1.5 g, 60 mmol) in N,N-dimethylformamide (30 mL), and the mixture was stirred at ambient temperature for 30 minutes. To the above solution was slowly added 2-trifluoromethylbenzyl chloride (5.0 g,25 mmol) in N,N-dimethylformamide (10 mL). The mixture was stirred at ambient temperature for 3 hours. After carefully quenching with water (100 mL), the mixture was extracted with ethyl acetate (3*100 mL). The ethyl acetate solution was washed with brine (2*100 mL) and dried over Na2 SO4. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (3:1 hexane/ethyl acetate) to give the title compound as a white solid (2.9 g, 41%). 1 H-NMR (300 MHz, CDCl3) delta 7.72 (d, J=7.8 Hz, 1 H), 7.68 (d, J=7.9Hz, 1 H), 7.56 (t, J=7.7 Hz, 1 H), 7.41 (t, J=7.7 Hz, 1 H), 6.39 (s, 1 H), 6.28 (s, 2 H), 5.22 (s, 2 H), 4.79 (s, 1 H), 2.27 (s, 3 H).
  • 73
  • [ 121-02-8 ]
  • [ 6153-39-5 ]
  • [ 197960-17-1 ]
YieldReaction ConditionsOperation in experiment
72% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenol <strong>[6153-39-5]Orcinol monohydrate</strong> (2.84 g, 20.0 mmol) and 2-methyl-5-nitrobenzenesulfonyl chloride (4.71 g, 20.0 mmol) were mixed in saturated aqueous NaHCO3 (60 mL) and diethyl ether (60 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (100 mL) and extracted into ethyl acetate (3*60 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a pale yellow solid (4.20 g, 72%). 1 H-NMR (300 MHz, CDCl3) delta 8.71 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 6.56 (s, 1H), 6.44 (s, 1H), 6.33 (s, 1H), 5.42 (s, 1H), 2.91 (s, 3H), 2.23 (s, 3H).
  • 74
  • [ 19040-62-1 ]
  • [ 6153-39-5 ]
  • [ 197960-04-6 ]
YieldReaction ConditionsOperation in experiment
72% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(2,5-Dimethylphenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 2,5-dimethylbenzenesulfonyl chloride (2.05 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (2.10 g, 72%). 1 H-NMR (300 MHz, CDCl3) delta 7.65 (s, 1H), 7.29 (m, 1H), 7.25 (m, 1H), 6.50 (s, 1H), 6.38 (s, 1H), 6.30 (s, 1H), 5.27 (br s, 1H), 2.30 (s, 3H), 2.18 (s, 3H), 2.03 (s, 3H).
  • 75
  • [ 54090-08-3 ]
  • [ 6153-39-5 ]
  • [ 222034-03-9 ]
YieldReaction ConditionsOperation in experiment
41% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(2-Chloro-5-trifluoromethylphenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 2-chloro-5-trifluoromethylbenzenesulfonyl chloride (2.79 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 3% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (1.50 g, 41%). 1 H-NMR (300 MHz, CDCl3) delta 8.24 (d, J=1.9 Hz, 1H), 7.83 (dd, J=8.3, 2.1 Hz, 1H), 7.76 (d, J=8.4 Hz, 1H), 6.57 (s, 1H), 6.55 (s, 1H), 6.46 (s, 1H), 5.07 (br s, 1H), 2.24 (s, 3H).
  • 76
  • [ 6153-39-5 ]
  • [ 82417-45-6 ]
  • [ 189341-21-7 ]
YieldReaction ConditionsOperation in experiment
55% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 2,3-Dichlorobenzenesulfonic acid 3-hydroxy-5-methylphenyl ester A solution of <strong>[6153-39-5]orcinol monohydrate</strong> (0.71 g, 5.0 mmol) and 2,3-dichlorobenzenesulfonyl chloride (1.23 g, 5.0 mmol) in saturated NaHCO3 (20 mL) and diethyl ether (20 mL was stirred at room temperature for 2 days. The reaction mixture was quenched with water (50 mL) and extracted with ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (methylene chloride to 2% ethyl acetate in methylene chloride) to give the title compound as a pale yellow oil (0.89 g, 55%). 1 H-NMR (300 MHz, CDCl3) delta 2.24 (s, 3H), 5.23 (s, 1H), 6.43 (t, 1H, J=2.2 Hz),6.54 (d, 2H, J=1.1 Hz), 7.34 (t, 1H, J=8.1 Hz), 7.75 (dd, 1H, J=0.8, 4.0 Hz), and 7.91 (dd, 1H, J=0.8, 4.0 Hz).
45% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(2,3-Dichlorophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 2,3-dichlorobenzenesulfonyl chloride (2.46 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a pale yellow solid (1.45 g, 45%). 1 H-NMR (300 MHz, CDCl3) delta 7.91 (d, J=8.0 Hz, 1 H), 7.75 (d, J=8.0 Hz, 1 H), 7.33 (t, J=8.0 Hz, 1 H), 6.55 (s, 2 H), 6.44 (s, 1 H), 5.27 (s, 1 H), 2.24 (s, 3 H).
  • 77
  • [ 6153-39-5 ]
  • [ 103008-51-1 ]
  • [ 197959-83-4 ]
YieldReaction ConditionsOperation in experiment
57% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 5-Methyl-3-(2-trifluoromethoxyphenylsulfonyloxy)phenol Orcinol monohydrate (1.42 g, 10.0 mmol) and 2-trifluoromethoxybenzenesulfonyl chloride (2.35 g, 9.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a yellow oil (1.80 g, 57%). 1 H-NMR (300 MHz, CDCl3) delta 7.96 (d, J=7.9 Hz, 1H), 7.72 (t, J=7.8 Hz, 1H), 7.50 (d, J=8.1 Hz, 1H), 7.40 (t, J=7.8 Hz, 1H), 6.55 (s, 1H), 6.52 (s, 1H), 6.41 (s, 1H), 5.04 (s, 1H); 2.23 (s, 3H).
  • 78
  • [ 84468-15-5 ]
  • [ 6153-39-5 ]
  • [ 197960-39-7 ]
YieldReaction ConditionsOperation in experiment
37% In diethyl ether; hexane; sodium hydrogencarbonate; b) 3-(5-Isoquinolinylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 5-isoquinolinesulfonyl chloride (2.64 g, 10.0 mmol), as prepared in the preceding step, were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was triturated from ether/hexane to give the title compound as a pale yellow solid (1.15 g, 37%). 1 H-NMR (300 MHz, CDCl3) delta 9.67 (s, 1H), 9.60 (s, 1H), 8.86 (d, J=6.1 Hz, 1H), 8.63 (d, J=8.2 Hz, 1H), 8.37 (t, J=6.1 Hz, 2H), 7.86 (t, J=7.8 Hz, 1H), 6.46 (s, 1H), 6.23 (s, 1H), 5.97 (s, 1H), 2.08 (s, 3H).
37% In diethyl ether; sodium hydrogencarbonate; b 3-(5-Isoquinolinylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 5-isoquinolinesulfonyl chloride (2.64 g, 10.0 mmol), as prepared in the preceding step, were mixed in saturated NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was triturated with ether/hexane to give the title compound as a pale yellow solid (1.15 g, 37%). 1H-NMR (300 MHz, CDCl3) delta9.67 (s, 1H), 9.60 (s, 1H), 8.86 (d, J=6.1 Hz, 1H), 8.63 (d, J=8.2 Hz, 1H), 8.37 (t, J=6.1 Hz, 2H), 7.86 (t, J=7.8 Hz, 1H), 6.46 (s, 1H), 6.23 (s, 1H), 5.97 (3, 1H), 2.08 (s, 3H).
  • 79
  • [ 42899-76-3 ]
  • [ 6153-39-5 ]
  • [ 197960-44-4 ]
YieldReaction ConditionsOperation in experiment
58% In dichloromethane; sodium hydrogencarbonate; a 5-Methyl-3-(3-pyridinylsulfonyloxy)phenol A mixture of <strong>[6153-39-5]orcinol monohydrate</strong> (1.42 g, 0.01 mol) and 3-pyridylsulfonyl chloride hydrochloride (2.13 g, 0.01 mol), as prepared in J. Am. Chem. Soc., 114:4889 (1992), in saturated aqueous sodium bicarbonate (17.5 mL) and dichloromethane (50 mL) was stirred rapidly at ambient temperature for 2 days. The dichloromethane was separated and the aqueous layer was extracted with ethyl acetate (3*25 mL). The ethyl acetate and dichloromethane extracts were combined and washed with brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was recrystallized from ether and hexane, collected by filtration, and dried under high vacuum to give 1.54 g of a white solid (58percent yield). 1 H-NMR (300 MHz, CDCl3) delta 9.03 (d, 1H), 8.88 (dd, 1H), 8.16 (dt, 1H), 7.5 (m, 1H), 6.57 (d, 1H), 6.42 (s, 1H), 6.32 (t, 1H), 2.24 (s, 3H).
  • 80
  • [ 6153-39-5 ]
  • [ 73713-79-8 ]
  • [ 197959-86-7 ]
YieldReaction ConditionsOperation in experiment
79% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(Benzo-2,1,3-thiadiazole-4-sulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and benzo-2,1,3-thiadiazole-4-sulfonyl chloride (2.35 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a pale yellow solid (2.55 g, 79%). 1 H-NMR (300 MHz, CDCl3) delta 8.34 (d, J=8.8 Hz, 1H), 8.26 (d, J=7.1 Hz, 1H), 7.72 (t, J=8.8 Hz, 1H), 6.53 (s, 1H), 6.47 (s, 1H), 6.37 (s, 1H), 5.24 (s, 1H), 2.19 (s, 1H).
  • 81
  • [ 197960-31-9 ]
  • [ 6153-39-5 ]
  • [ 197960-32-0 ]
YieldReaction ConditionsOperation in experiment
69% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; c) 3-(2-Cyano-5-methylphenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 2-cyano-5-methylbenzene-sulfonyl chloride (2.0 g, 9.0 mmol), as prepared in the preceding step, were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 4% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (2.1 g, 69%). 1 H-NMR (300 MHz, CDCl3) delta 7.91 (s, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.57 (d, J=7.9 Hz, 1H), 6.59 (s, 1H), 6.58 (s, 1H), 6.51 (s, 1H), 5.61 (s, 1H), 2.51 (s, 3H), 2.29 (s, 3H).
  • 82
  • [ 85-46-1 ]
  • [ 6153-39-5 ]
  • [ 189340-49-6 ]
YieldReaction ConditionsOperation in experiment
68% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 5-Methyl-3-(1-naphthalenylsulfonyloxy)phenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10.0 mmol) and 1-naphthalenesulfonyl chloride (2.27 g, 10.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2 SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 3% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (2.15 g, 68%). 1 H-NMR (300 MHz, CDCl3) delta 8.79 (d, J=8.5 Hz, 1H), 8.14 (d, J=7.0 Hz, 2H), 7.98 (d, J=8.4 Hz, 1H), 7.78 (t, J=8.5 Hz, 1H), 7.67 (t, J=8.1 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 6.46 (s, 1H), 6.34 (s, 1H), 6.17 (s, 1H), 2.14 (s, 3H).
  • 83
  • [ 611-17-6 ]
  • [ 6153-39-5 ]
  • [ 189340-05-4 ]
YieldReaction ConditionsOperation in experiment
With NaH; In hexane; N,N-dimethyl-formamide; b 3-(2-Chlorobenzyloxy)-5-methylphenol To 1.31 g (9.22 mmol) of <strong>[6153-39-5]orcinol monohydrate</strong> in 20 mL anhydrous N,N-dimethylformamide under a nitrogen atmosphere was added 220 mg (9.17 mmol) of NaH (100%). After 5 min, 1.30 mL (10.0 mmol) of 2-chlorobenzyl bromide was added. The reaction mixture was stirred for 2 h and then quenched with 1N HCl. The reaction mixture was extracted into ethyl acetate (200 mL). The organic phase was washed with water (4*100 mL), dried (MgSO4), and concentrated in vacuo. Purification by flash chormatography (diethyl ether/hexane (50:50 to 100:0) gave 656 mg of the title compound as a glass. 1 H-NMR (300 MHz, CDCl3) delta 7.54 (dd, 1H, J=3, 7 Hz), 7.39 (dd, 1H, J=3, 7 Hz), 7.2-7.3 (m, 2H), 6.41 (s, 1H), 6.29-6.30 (m, 2H), 5.29 (s, 2H), and 2.28 (s, 3H).
With NaH; In hexane; N,N-dimethyl-formamide; a 3-(2-Chlorobenzyloxy)-5-methylphenol To 1.31 g (9.22 ?mmol) of <strong>[6153-39-5]Orcinol monohydrate</strong> in 20 mL anhydrous DMF under a nitrogen atmosphere was add ed 220 mg (9.17 mmol) of NaH (100%). After 5 min, 1.3 mL (100 mmol) of 2-chlorobenzyl bromide was added. The reaction mixture was stirred for 2 h and then quenched with 1N HCl. The reaction mixture was extracted into ethyl acetate (200 mL). The organic phase was washed with H2 O (4*100 mL), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (ether/hexane (50:50 to 100:0) gave 656 mg of the title compound as a hardened oil. 1 H-NMR (300 MHz, CDCl3) delta 7.54 (dd, 1H, J=3, 7 Hz), 7.39 (dd, 1H, J=3, 7 Hz), 7.2 -7.3 (m, 2H), 6.41 (s, 1H), 6.29-6:30 (m, 2H), 5.29 (s, 2H), and 2.28 (s, 3H).
  • 84
  • [ 6153-39-5 ]
  • [ 20982-28-9 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride; In pyridine; ethyl acetate; (1) <strong>[6153-39-5]Orcinol monohydrate</strong> (50 g) is dissolved in pyridine (400 ml), and thereto is added acetic anhydride (133 ml), and the mixture is stirred at room temperature for 17 hours. The reaction mixture is concentrated under reduced pressure, and the resulting residue is dissolved in ethyl acetate (500 ml). The mixture is washed successively with 10% hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure to give orcinol diacetate (74 g). EI-MS (m/z): 208 (M+) NMR (CDCl3) delta:2.27 (6H, s), 2.35 (3H, s), 6.71 (1H, t, J=1.8), 6.80 (2H, m)
  • 85
  • [ 98-88-4 ]
  • [ 6153-39-5 ]
  • [ 104311-36-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; EXAMPLE 29 5-Methyl-benzene-1,3-diol dibenzoate The synthesis of this compound proceeded in the same fashion as in Example 1 using 1.42 g (0.01 mol) of <strong>[6153-39-5]orcinol monohydrate</strong>, 2.23 g (0.022 mol) of triethylamine and 2.81 g (0.02 mol) of benzoyl chloride. The product amounted to 2.78 g, m.p. 80-83 C. Elemental analysis for C21 H16 O4: Calc'd: C, 75.89; H, 4.85; Found: C, 75.49; H, 5.04.
  • 86
  • [ 111-92-2 ]
  • [ 6153-39-5 ]
  • 3-dibutylamino-5-methylphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% EXAMPLE IV A 300 milliliter Parr minibomb was charged with <strong>[6153-39-5]orcinol monohydrate</strong>, 42 grams, 0.3 mole and di-n-butylamine, 128 milliliters. The bomb was sealed and heated to 200 C. At this temperature the internal pressure of the bomb was 90 pounds per square inch as registered on the gauge. After 48 hours at 200, the bomb was cooled and the light brown syrup analyzed by thin-layer chromatography. The excess di-n-butylamine was removed by distillation at 20 Torr and the product was further purified by filtration through a silica gel column using ethyl acetate as the eluent. The product 3-dibutylamino-5-methylphenol was isolated in 61% yield: 43 grams.
  • 87
  • [ 931-20-4 ]
  • [ 6153-39-5 ]
  • 2-(N-Methyl-1,2,3,4-tetrahydro-pyridin-4-yl)-5-(methyl)-resorcinol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In acetic acid; EXAMPLE IX 2-(N-Methyl-1,2,3,4-tetrahydro-4-pyridyl)-5-(methyl) resorcinol <strong>[6153-39-5]Orcinol hydrate</strong> (15 g) and N-methylpiperidone (11.0 g) were dissolved in 30 ml acetic acid and treated with HCl gas as described in Example VI giving 6.42 g of product, m.p. 241-243.
  • 88
  • [ 6153-39-5 ]
  • [ 71681-91-9 ]
YieldReaction ConditionsOperation in experiment
With sodium; In methanol; EXAMPLE 4 Preparation of the Monosodium Salt of 5-Methylresorcinol <strong>[6153-39-5]5-Methylres<strong>[6153-39-5]orcinol monohydrate</strong></strong> (14.2 grams; 0.10 moles) dissolved in methanol (20 ml) was charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was blanketed with nitrogen gas, and sodium methoxide prepared by combining sodium (2.3 grams) with methanol (40 ml) was added with stirring. The reaction mixture was then heated at 50 C. with continued stirring for a period of about 15 minutes. After this time the reaction mixture was stripped of solvent under reduced pressure to yield the desired product as a grey solid.
  • 89
  • [ 6153-39-5 ]
  • [ 1694-92-4 ]
  • [ 208643-52-1 ]
YieldReaction ConditionsOperation in experiment
5.67 g (61%) With sodium hydrogencarbonate; In diethyl ether; a 2-(2-Nitrophenylsulfonyloxy)phenol A mixture of <strong>[6153-39-5]orcinol monohydrate</strong> (4.32 g, 30.2 mmol) and 2-nitrobenzenesulfonyl chloride (6.65 g, 30.0 mmol) in diethyl ether (100 mL) and saturated NaHCO3 (100 mL) was stirred at ambient temperature for 36 h. The reaction mixture was diluted with water (100 mL) and extracted into 10% tetrahydrofuran/ethyl acetate, dried (MgSO4), and concentrated. The residue was diluted with diethyl ether (150 mL) and the resulting disulfonated product (1.6 g) removed by filtration. The filtrate was concentrated and purified by flash chromatography (3:97 to 10:90 diethyl ether/dichloromethane) to give 5.67 g (61%) of the title compound as an oil. 1H-NMR (300 MHz, CDCl3) delta7.99 (dd, 1H, J=7, 2 Hz), 7.79-7.86 (m, 2H), 7.65-7.73 (m, 1H), 6.60-6.61 (m, 1H), 6.58-6.59 (m, 1H), 6.50-6.51 (m, 1H), 5.32 (s, 1H), 2.25 (s, 3H).
  • 90
  • [ 6153-39-5 ]
  • [ 189339-69-3 ]
YieldReaction ConditionsOperation in experiment
71% In diethyl ether; dichloromethane; sodium hydrogencarbonate; ethyl acetate; a 3-(2-Chlorophenylsulfonyloxy)-5-methylphenol <strong>[6153-39-5]Orcinol monohydrate</strong> (1.42 g, 10 mmol) and 2-chlorobenezenesulfonyl chloride (2.43 g, 11 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously and extracted into ethyl acetate (3*50 mL). The organic phase was washed with brine (2*50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane) to give the title compound as a pale-yellow liquid (2.15 g, 71%). 1H-NMR (300 MHz, CDCl3) delta2.22 (s, 3H), 5.24 (s, 1H), 6.43 (s, 1H), 6.52 (s, 2H), 7.38 (m, 1H), 7.60 (m, 2H), and 7.96 (dd, 1H,J=3.9, 0.6 Hz).
YieldReaction ConditionsOperation in experiment
The compounds of formula (VI) that are particularly preferred are chosen from: ... 5-methylpyrogallol 4-methoxyresorcinol 3,5-dihydroxytoluene monohydrate 4-propylresorcinol ...
  • 92
  • [ 6153-39-5 ]
  • O-[ 3-(2,2-Dimethoxyethoxy)-5-methylphenyl] N,N-Dimethylcarbamate [ No CAS ]
  • 93
  • [ 6153-39-5 ]
  • O-[3-(2,2-dimethoxyethoxy)-5-methylphenyl] N-methylcarbamate [ No CAS ]
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