15980-22-0|4-Amino-2,6-dimethylphenol| Ambeed

CAS No. :	15980-22-0
Formula :	C₈H₁₁NO
M.W :	137.18
SMILES Code :	OC1=C(C)C=C(N)C=C1C
MDL No. :	MFCD10039560
InChI Key :	OMVFXCQLSCPJNR-UHFFFAOYSA-N
Pubchem ID :	82668

Safety of [ 15980-22-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 15980-22-0 ]

* 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 [ 15980-22-0 ]

[ 15980-22-0 ] Synthesis Path-Downstream 1~54

1
[ 13331-93-6 ]
[ 15980-22-0 ]

References: [1]Helvetica Chimica Acta,1939,vol. 22,p. 267,271.
[2]Bulletin de la Societe Chimique de France,1959,p. 1275,1280.
[3]Journal of the Society of Chemical Industry,1931,vol. 50,p. 79 T.
[4]Organic and Biomolecular Chemistry,2008,vol. 6,p. 354 - 358.

2
[ 15980-22-0 ]
[ 98-88-4 ]
N-(4-hydroxy-3,5-dimethylphenyl)benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 6348 - 6358.
[2]Helvetica Chimica Acta,1939,vol. 22,p. 267,271.

3
[ 1778-65-0 ]
[ 15980-22-0 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 1036,1040.

4
[ 68048-41-9 ]
[ 15980-22-0 ]
[ 72600-10-3 ]

References: [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 775 - 784.
[2]Chemistry Letters,1979,p. 1077 - 1080.

5
[ 15980-22-0 ]
[ 115607-76-6 ]
3-butyryl-4-(4-hydroxy-3,5-dimethylphenylamino)-8-methoxyquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In 1,4-dioxane; methanol; chloroform;	B. Preparation of 3-butyryl-4-(3,5-dimethyl-4-hydroxyphenylamino)-8-methoxyquinoline 2,6-Dimethyl-4-aminophenol (0.78 g, 5.69 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (1.0 g, 3.79 mmol) in dioxan (35 ml) were refluxed under nitrogen for 2.5 hours. The solvent was evaporated, and the residue treated with saturated sodium bicarbonate solution and chloroform. The resulting solid was filtered, washed with chloroform and water, boiled in methanol and filtered again to give the title compound (0.84 g) m.p. 287-9 (dec). Found; C 71.01, H 6.49, N 7.43. Requires; C 71.00, H 6.50, N 7.50.

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2748 - 2762.
[2]Patent: US5143920,1992,A .

6
[ 15980-22-0 ]
[ 98-60-2 ]
4-chloro-N-(4-hydroxy-3,5-dimethylphenyl)benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.
[2]Russian Journal of Organic Chemistry,1998,vol. 34,p. 210 - 220.

7
[ 15980-22-0 ]
[ 98-09-9 ]
[ 50994-42-8 ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 6348 - 6358.
[3]Russian Journal of Organic Chemistry,1998,vol. 34,p. 210 - 220.

8
[ 15980-22-0 ]
[ 98-59-9 ]
[ 14034-15-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine; at 0 - 20℃; for 5h;Inert atmosphere;	General procedure: The para-amino-phenol (1.06 mmol) was dissolved in dry pyridine (2 mL) and cooled to 0 C. para-Toluenesulfonyl chloride (0.244 g, 1.28 mmol) was added in small portions; the mixture was warmed to room temperature, and stirred under argon for 5 h. The reaction mixture was diluted with Et2O and washed successively with water, 5% HCl (aq), water, and brine. The organic layer wasdried over anhydrous MgSO4, filtered, and concentrated to yield the crude sulfonamide. The product was purified by silica gel column chromatography using hexanes/EtOAc (9.5:0.5) as eluent. Compound 6a: mp: 138e139.2 C (lit.38 mp 143e145 C).

References: [1]Tetrahedron,2014,vol. 70,p. 6963 - 6973.
[2]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.
[3]Russian Journal of Organic Chemistry,1998,vol. 34,p. 210 - 220.

9
[ 54997-90-9 ]
[ 15980-22-0 ]
N-(4-hydroxy-3,5-dimethyl-phenyl)-4-isopropyl-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

10
[ 15980-22-0 ]
[ 21926-53-4 ]
[4-(4-hydroxy-3,5-dimethyl-phenylsulfamoyl)-phenyl]-carbamic acid methyl ester [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

11
[ 15980-22-0 ]
[ 98-68-0 ]
N-(4-hydroxy-3,5-dimethyl-phenyl)-4-methoxy-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

12
[ 15980-22-0 ]
[ 98-58-8 ]
4-bromo-N-(4-hydroxy-3,5-dimethyl-phenyl)-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

13
[ 15980-22-0 ]
[ 98-74-8 ]
N-(4-hydroxy-3,5-dimethyl-phenyl)-4-nitro-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

14
[ 15980-22-0 ]
[ 4655-44-1 ]
N'-(4-bromophenylsulfonyl)-N-(4-hydroxy-3,5-dimethylphenyl)benzimidamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 991 - 1000.

15
[ 15980-22-0 ]
N-(1-chloro-ethylidene)-4-methyl-benzenesulfonamide [ No CAS ]
N-[1-(4-hydroxy-3,5-dimethyl-phenylamino)-ethylidene]-4-methyl-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 991 - 1000.

16
[ 15980-22-0 ]
[ 116133-09-6 ]
4-[4-(4-amino-2,6-dimethyl-phenoxy)-6-chloro-[1,3,5]triazin-2-ylamino]-benzonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2229 - 2234.

17
[ 15980-22-0 ]
[ 4513-25-1 ]
N-[1-(4-Hydroxy-3,5-dimethyl-phenylamino)-1-phenyl-meth-(E)-ylidene]-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 991 - 1000.

18
[ 937-32-6 ]
[ 15980-22-0 ]
C₁₄H₁₂N₂O₃S [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 1121 - 1128.
[2]Russian Journal of Organic Chemistry,2004,vol. 40,p. 1291 - 1294.
[3]Magnetic Resonance in Chemistry,2008,vol. 46,p. 811 - 817.

19
[ 933-00-6 ]
[ 15980-22-0 ]
N-[(4-methylphenyl)thio]-2,6-dimethyl-1,4-benzoquinone imine [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 1121 - 1128.
[2]Russian Journal of Organic Chemistry,2008,vol. 44,p. 231 - 236.

20
[ 1950-65-8 ]
[ 15980-22-0 ]
N-[(4-methoxyphenyl)thio]-2,6-dimethyl-1,4-benzoquinone imine [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 1121 - 1128.
[2]Russian Journal of Organic Chemistry,2008,vol. 44,p. 231 - 236.
[3]Magnetic Resonance in Chemistry,2008,vol. 46,p. 811 - 817.

21
[ 15980-22-0 ]
[ 931-59-9 ]
[ 41772-29-6 ]

References: [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 1121 - 1128.
[2]Russian Journal of Organic Chemistry,2008,vol. 44,p. 231 - 236.

22
[ 15980-22-0 ]
[ 933-01-7 ]
N-[(4-chlorophenyl)thio]-2,6-dimethyl-1,4-benzoquinone imine [ No CAS ]

23
[ 15980-22-0 ]
[ 956011-64-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of 34.5 g of morpholin-4-yl acetic acid hydrochloride from Example 1a) (MW = 181.6; 190 mmol) in 500 ml of dichloro- methane were added 42 g of 4-dimethylaminopyridine (MW = 122.17; 344 mmol) and, after a few minutes, 71 g of N.N'-dicyclohexylcarbo- diimide (MW = 206.33, 344 mmol).23.3 g of <strong>[15980-22-0]4-amino-2,6-dimethylphenol</strong> from Example 1b) (MW = 137.18; 170 mmol) were added to the stirred mixture under a <n="8"/>nitrogen atmosphere and at room temperature.The mixture was stirred for 24 hours, after which the solid formed was removed by filtration. The solution was then concentrated under reduced pressure. The residue was taken up with a hexane/ethyl acetate 1 :1 mixture and filtered again through a layer of silica.The resulting solution was concentrated under reduced pressure and the residue was purified by flash chromatography on silica, using a chloroform/methanol 9:1 mixture as eluent.The solid residue thus obtained was N-(4-hydroxy-3,5-dimethyl- phenyl)-2-morpholin-4-yl acetamide, which was crystallized twice from ethyl acetate and then used in the subsequent reactions without further purification.

References: [1]Patent: WO2007/124832,2007,A1 .Location in patent: Page/Page column 6-7.

24
[ 15980-22-0 ]
(4-amino-2,6-dimethyl-phenoxy)-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1185 - 1187.

25
[ 15980-22-0 ]
(R)-N-{(1R,3R,4R)-4-[2-(4-Amino-2,6-dimethyl-phenoxy)-acetylamino]-1-benzyl-3-hydroxy-5-phenyl-pentyl}-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1185 - 1187.

26
[ 15980-22-0 ]
[ 308291-68-1 ]

References: [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 991 - 1000.

27
[ 15980-22-0 ]
[ 308291-75-0 ]

References: [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 991 - 1000.

28
[ 15980-22-0 ]
N-[1-(3,5-dimethyl-4-oxo-cyclohexa-2,5-dienylideneamino)-ethylidene]-4-methyl-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 991 - 1000.

29
[ 15980-22-0 ]
N-[1-(3,5-dimethyl-4-oxo-cyclohexa-2,5-dienylideneamino)-ethylidene]-4-methyl-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 991 - 1000.

30
[ 15980-22-0 ]
[ 66660-44-4 ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.
[2]Russian Journal of Organic Chemistry,1998,vol. 34,p. 210 - 220.

31
[ 15980-22-0 ]
[ 14034-17-4 ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.
[2]Russian Journal of Organic Chemistry,1998,vol. 34,p. 210 - 220.
[3]Tetrahedron,2014,vol. 70,p. 6963 - 6973.

32
[ 15980-22-0 ]
[ 216066-04-5 ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.
[2]Russian Journal of Organic Chemistry,1998,vol. 34,p. 210 - 220.

33
[ 15980-22-0 ]
N-(3,5-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-4-methoxy-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

34
[ 15980-22-0 ]
4-bromo-N-(3,5-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

35
[ 15980-22-0 ]
N-(3,5-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-4-nitro-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

36
[ 15980-22-0 ]
N-(3,5-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-4-isopropyl-benzenesulfonamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

37
[ 15980-22-0 ]
[4-(3,5-dimethyl-4-oxo-cyclohexa-2,5-dienylidenesulfamoyl)-phenyl]-carbamic acid methyl ester [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527.

38
[ 1435-62-7 ]
[ 15980-22-0 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 1036,1040.

39
[ 527-61-7 ]
[ 15980-22-0 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 1036,1040.
[2]Tetrahedron,2014,vol. 70,p. 6963 - 6973.

40
[ 3096-70-6 ]
[ 15980-22-0 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 1036,1040.

41
[ 15980-22-0 ]
[ 75-87-6 ]
5-hydroxy-4,6-dimethyl-1H-indole-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5-Hydroxy-4,6-dimethyl-1H-indole-2,3-dione was prepared from <strong>[15980-22-0]3,5-dimethyl-4-hydroxyaniline</strong> according to Procedure A: 1H NMR (DMSO-d6): δ 2.17 (s, 3H), 2.30 (s, 3H), 6.45 (s, 1H), 8.29 (s, 1H), 10.65 (s, 1H); ESI-MS m/z 190 (M-H)-

References: [1]Patent: US6350747,2002,B1 .Location in patent: Page column 67.

42
[ 2423-71-4 ]
[ 15980-22-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogen;palladium 10% on activated carbon; In ethanol; under 1125.11 Torr; for 1h;	A solution of 1 g (6 mmol) of 2,6-dimethyl-4-nitrophenol in 20 ml of ethanol is placed under 1.5 bar of hydrogen in the presence of 10% Pd/C for 1 hour. The Pd/C is eliminated by filtration on celite and the filtrate is concentrated under reduced pressure. The evaporation residue crystallizes spontaneously, it is washed twice with 50 ml of heptane and dried overnight under vacuum. A cream coloured solid is obtained with a yield of 86%. [00525] Melting point: 139-140 C.
85%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 2250.23 Torr;	Step 1: 4-amino-2,6-dimethyl-phenol; 3.00 g (18.0 mmol) 2,6-dimethyl-4-nitrophenol were hydrogenated with 0.50 g palladium on charcoal (Pd/C, 10%) in 50 mL MeOH in a 3 bar hydrogen atmosphere at RT. After the end of the reaction the catalyst was suction filtered and the filtrate was concentrated by rotary evaporation. The residue was triturated with DIPE and the precipitate was suction filtered and dried i. vac.Yield: 2.10 g (85% of theory)ESI-MS: m/z=138 (M+H)+ Rf: 0.5 (silica gel: DCM/MeOH/cyc/NH4OH=70:15:15:2)
79%	With hydrogenchloride; tin; acetic acid; at 20℃; for 48h;	4-Amino-2,6-dimethylphenol (15). Thesynthesis was carried out according to the methodology described in theliterature.5 2,6-Dimethyl-4-nitrophenol (0.60 g, 3.0 mmol), solidtin (1.14 g, 9.6 mmol), hydrochloric acid (0.72 mL), and acetic acid (7.2 mL)were placed in a round-bottomed flask. The system was kept under magneticstirring for 48 h at room temperature. Distilled water (60 mL) and aqueousNaHCO3 were added for neutralization and the product was extractedfrom the aqueous phase with ethyl acetate (100 mL). The organic phase waswashed with aqueous saturated NaHCO3, dried with MgSO4,filtered, and rotary-evaporated. The product was a red solid (0.33 g; 79% yield) withm.p. 107-109 C. IR (KBr, ν max/cm-1):3420, 3388 (N-H), 2949, 2919, 2853 (C-H), 1632, 1487 (C=C), 1234, 1205 (C-O,C-N). 1H NMR (200 MHz, CDCl3) δ/ppm: 7.13 (1H, s, OH), 6.15 (2H, s, Ar-H), 4.30 (2H, s,NH2), 2.01 (6H, s, 2×CH3).

	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 4h;	A suspension of 50 g of 4-nitro-2,6-dimethylphenol (MW=167.16; 294.5 mmol) and 5 g of 10% palladium-on-charcoal (MW=106.41; 4.7 mmol) in 1000 ml of ethanol was stirred at room temperature under a hydrogen atmosphere in a Parr hydrogenator for 4 hours. The mixture was then filtered under nitrogen through a layer of Celite and the solvent was evaporated off under reduced pressure.The solid residue thus obtained was 4-amino-2,6-dimethylphenol (38 g), which was used in subsequent reactions without further purification.LC/MS (M+H)+=138; 123 (base peak).1H-NMR (δ, DMSO d-6) 7.5-6.8 (broad s, 1H); 6.16 (s, 2H); 4.5-3.9 (broad s, 2H); 2.03 (s, 6H).
	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 4h;	A suspension of 50 g of 4-nitro-2,6-dimethylphenol (MW = 167.16; 294.5 mmol) and 5 g of 10% palladium-on-charcoal (MW = 106.41 ; 4.7 mmol) in 1000 ml of ethanol was stirred at room temperature under a hydrogen atmosphere in a Parr hydrogenator for 4 hours. The mixture was then filtered under nitrogen through a layer of Celite and the solvent was evaporated off under reduced pressure.The solid residue thus obtained was 4-amino-2,6-dimethylphenol (38 g), which was used in subsequent reactions without further purification.LC/MS (M+H)+ = 138; 123 (base peak).1H-NMR (δ, DMSO d-6) 7.5-6.8 (broad s, 1 H); 6.16 (s, 2H); 4.5-3.9 (broad s, 2H); 2.03 (s, 6H).

References: [1]Organic Letters,2019,vol. 21,p. 1315 - 1319.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 6348 - 6358.
[3]Patent: US6653312,2003,B1 .Location in patent: Page/Page column 44.
[4]Patent: US2012/88755,2012,A1 .Location in patent: Page/Page column 59.
[5]Tetrahedron Letters,2015,vol. 56,p. 4733 - 4736.
[6]Organometallics,2021,vol. 40,p. 107 - 118.
[7]Patent: US2009/137593,2009,A1 .Location in patent: Page/Page column 2.
[8]Chemical Communications,2013,vol. 49,p. 9591 - 9593.
[9]Journal of Materials Chemistry A,2015,vol. 3,p. 6187 - 6195.
[10]Patent: WO2007/124832,2007,A1 .Location in patent: Page/Page column 6.

43
[ 15980-22-0 ]
5-hydroxy-4,6-dimethyl-1H-indole-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 94 5-Hydroxy-4,6-dimethyl-1H-indole-2,3-dione 3-[N-(4-methylphenyl)hydrazone] 5-Hydroxy-4,6-dimethyl-1H-indole-2,3-dione was prepared from <strong>[15980-22-0]3,5-dimethyl-4-hydroxyaniline</strong> according to Procedure A: 1H NMR (DMSO-d6): δ2.17 (s, 3H), 2.30 (s, 3H), 6.45 (s, 1H), 8.29 (s, 1H), 10.65 (s, 1H); ESI-MS m/z 190 (M-H)-.

References: [1]Patent: US6369086,2002,B1 .

44
[ 3314-35-0 ]
[ 15980-22-0 ]
[ 133356-67-9 ]
4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)amino-2,6-dimethylphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In dichloromethane;	Example D 2,6-dimethyl-4-(1-phenyl-1H-pyrazol-3-yl)aminophenol <strong>[15980-22-0]2,6-dimethyl-4-aminophenol</strong> (15 g) and 4,5-dihydro-1-phenyl-1H-pyrazol-3-amine (17.6 g) were heated with p-toluene sulfonic acid (0.2 g) at 160 for 1 hour under nitrogen. The mix was cooled, taken up in dichloromethane and washed with dilute HCl, and water. Evaporation, and chromatography of the residue (silica, dichloromethane/ethyl acetate [9:1]) gave 4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)amino-2,6-dimethylphenol (14.2 g), mp 154-158. This was refluxed in toluene (40 ml) with 10% palladium on charcoal (10 g) for 3 hours. The mixture was filtered and evaporated to give, after crystallisation from cyclohexane/ethyl acetate, the title compound (8 g), mp 154-155.

References: [1]Patent: US5428044,1995,A .

45
ethyl acetate n-hexane [ No CAS ]
[ 15980-22-0 ]
[ 5254-23-9 ]
[ 814-49-3 ]
[ 130211-48-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile;	EXAMPLE 3 Under ice-cooling, to a solution of 0.9 g of 3,7,11-trimethyl-(2Z,6E)-2,6,10-dodecatrienoic acid in 10 m of acetonitrile are added 578 mg of triethylamine, then 854 mg of diethylphosphorochloridate. After the mixture is stirred for 30 minutes, 522 mg of <strong>[15980-22-0]4-amino-2,6-dimethylphenol</strong> is added and the reaction mixture is stirred at room temperature. Ice chips are added into the reaction mixture, the mixture is extracted with isopropyl ether and the extracted with 10% hydrochloric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, followed by drying and then evaporation of the solvent. The residue is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (1:3)] to give 580 mg of 4-[3,7,11-trimethyl-(2Z,6E)-2,6,10-dodecatrienoylamino]-2,6-dimethylphenol Mass (m/e): 335 (M+), 286, 219, 137, Liquid, IR νmax (cm-1): 3310, 1660. NMR (CDCl3) δ: 1.59 (s, 3H), 1.61 (s, 3H), 1.67 (s, 3H), 1.87 (d, 1.5Hz, 3H), 2.04 (m, 4H), 2.19 (s, 6H), 2.26 (t, 8Hz, 2H), 2.70 (t, 8Hz, 2H), 5.0 to 5.2 (m, 2H), 5.65 (d, 1.5Hz, 1H), 7.07 (s, 2H).

References: [1]Patent: US5047555,1991,A .

46
[ 576-26-1 ]
[ 121-57-3 ]
[ 15980-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; sodium carbonate; sodium nitrite; In water;	A. Preparation of 2,6-dimethyl-4-aminophenol Sulphanilic acid (43.3 g, 0.25 mol) and sodium carbonate (13.25 g, 0.125 mol) were dissolved in water (250 ml) and cooled to 15 C. Sodium nitrite (18.63 g, 0.27 mol) in water (100 ml) was added in one portion, and the mixture added immediately to concentrated hydrochloric acid (53 ml) and ice (300 g), with stirring. After 30 minutes, the resulting suspension was added to an ice-cold solution of 2,6-dimethylphenol (30.54 g, 0.25 mol) and sodium hydroxide (55 g) in water (550 ml), stirring vigorously. After 2 hours, the temperature was raised to 50, and sodium dithionite (115 g, 0.66 mol) added portionwise. On heating to 75 the red colour discharged, and after a further 10 minutes, the solution was cooled to room temperature. The resulting white solid was filtered, washed and dried to give the title compound (27.33 g), m.p. 135-7.

References: [1]Patent: US5143920,1992,A .

47
[ 4972-29-6 ]
[ 15980-22-0 ]
[ 41772-29-6 ]

References: [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474.

48
[ 5184-27-0 ]
[ 15980-22-0 ]
[ 41772-29-6 ]

References: [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474.

49
[ 27691-42-5 ]
[ 15980-22-0 ]
N-[(4-chlorophenyl)thio]-2,6-dimethyl-1,4-benzoquinone imine [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474.

50
[ 5184-31-6 ]
[ 15980-22-0 ]
C₁₄H₁₂N₂O₃S [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474.

51
[ 5184-33-8 ]
[ 15980-22-0 ]
C₁₄H₁₂N₂O₃S [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474.

52
[ 15980-22-0 ]
[ 13088-17-0 ]
C₁₄H₁₂N₂O₃S [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474.

53
[ 4972-29-6 ]
[ 15980-22-0 ]
[ 1104591-33-4 ]

References: [1]Russian Journal of Organic Chemistry,2008,vol. 44,p. 231 - 236.

54
[ 15980-22-0 ]
[ 89531-58-8 ]
[ 956011-64-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h;	To a suspension of 34.5 g of morpholin-4-yl acetic acid hydrochloride from Example 1a) (MW=181.6; 190 mmol) in 500 ml of dichloro-methane were added 42 g of 4-dimethylaminopyridine (MW=122.17; 344 mmol) and, after a few minutes, 71 g of N,N'-dicyclohexylcarbo-diimide (MW=206.33, 344 mmol).23.3 g of 4-amino-2,6-dimethylphenol from Example 1b) (MW=137.18; 170 mmol) were added to the stirred mixture under a nitrogen atmosphere and at room temperature.The mixture was stirred for 24 hours, after which the solid formed was removed by filtration. The solution was then concentrated under reduced pressure. The residue was taken up with a hexane/ethyl acetate 1:1 mixture and filtered again through a layer of silica.The resulting solution was concentrated under reduced pressure and the residue was purified by flash chromatography on silica, using a chloroform/methanol 9:1 mixture as eluent.The solid residue thus obtained was N-(4-hydroxy-3,5-dimethyl-phenyl)-2-morpholin-4-yl acetamide, which was crystallized twice from ethyl acetate and then used in the subsequent reactions without further purification.

References: [1]Patent: US2009/137593,2009,A1 .Location in patent: Page/Page column 2-3.

Historical Records

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Friedel-Crafts Reaction • Halogenation of Phenols • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Leuckart-Wallach Reaction • Mannich Reaction • Oxidation of Phenols • Pechmann Coumarin Synthesis • Petasis Reaction • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reimer-Tiemann Reaction • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction • Vilsmeier-Haack Reaction

Related Functional Groups of
[ 15980-22-0 ]

Aryls

A205732 [17672-22-9]

2-Amino-6-methylphenol

Similarity: 0.90

A362852 [41458-65-5]

2-Amino-4,6-dimethylphenol

Similarity: 0.90

Amines

A362852 [41458-65-5]

2-Amino-4,6-dimethylphenol

Similarity: 0.90

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CAS No.: 15980-22-0

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