[ CAS No. 6214-44-4 ] {[proInfo.proName]}

Name: 6214-44-4|(4-Ethoxyphenyl)methanol|98%
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Quality Control of [ 6214-44-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6214-44-4 ]

Product Details of [ 6214-44-4 ]

CAS No. :	6214-44-4	MDL No. :	MFCD00004655
Formula :	C₉H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UKFLLQIRBABMKF-UHFFFAOYSA-N
M.W :	152.19	Pubchem ID :	80345
Synonyms :

Calculated chemistry of [ 6214-44-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.87
TPSA :	29.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	1.47
Log Po/w (WLOGP) :	1.43
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	2.0
Consensus Log Po/w :	1.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	1.85 mg/ml ; 0.0122 mol/l
Class :	Very soluble
Log S (Ali) :	-1.7
Solubility :	3.07 mg/ml ; 0.0202 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.74
Solubility :	0.276 mg/ml ; 0.00181 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 6214-44-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6214-44-4 ]

* 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.

Upstream synthesis route of [ 6214-44-4 ]
Downstream synthetic route of [ 6214-44-4 ]

[ 6214-44-4 ] Synthesis Path-Upstream 1~5

1
[ 6214-44-4 ]
[ 6653-80-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333 - 0.166667 h;	Example 14 Preparation of 4-Ethoxybenzyl Chloride Thionyl chloride (10.4g, 87.7mmol) was added dropwise to a 0° C. solution of 4-ethoxybenzyl alcohol (11.0 g, 72.4mmol) in dry CH2Cl2 (150 mL) with a catalytic amount of DMF (1 mL). Upon addition, reaction was allowed to stir for 5-10 minutes, while monitoring through TLC (CH₂Cl₂) for completion. Reaction mixture was concentrated under reduced pressure and the residue dissolved in minimal THF and then precipitated in cold H₂O to yield a white precipitate. The solid was collected, taken up in CH₂Cl₂, dried and concentrated. The resulting oil was solidified by cooling with CO₂/acetone. The compound as a white solid, which decomposes upon melting 11.3 g(92percent). ¹H NMR (300 MHz, CDCl3) δ=7.28 (d, 2H, J=6.6 Hz), 6.86 (d, 2H, J=6.6 Hz), 4.55 (s, 2H), 4.01 (q, 2H, J=6.9 Hz), 1.40 (t, 3H, J=6.9 Hz). ¹³C NMR (75 MHz, CDCl3) δ=159.0, 130.2, 129.7, 114.8, 63.7, 46.6, 15.0.
7.66 g	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 0.5 h; Inert atmosphere; Cooling with ice	Under an argon stream, p-Ethoxybenzyl alcohol (1) (6.509, 42.7 mmol) Of anhydrous methylene chloride (90 mL), The mixed solution of anhydrous N, N-dimethylformamide (70 L) was cooled with ice, Thionyl chloride (4.0 mL, 55.7 mmol) was added, And stirred for 30 minutes. The reaction solution was concentrated and dissolved in tetrahydrofuran (30 mL) Was added dropwise to ice water (150 mL). It was extracted twice with methylene chloride (50 mL) The obtained organic layer was dried with sodium sulfate, By concentrating under reduced pressure, To give compound 2 (7.66 g) as a pale yellow liquid.

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4861 - 4868
[2] Patent: US2006/88499, 2006, A1, . Location in patent: Page/Page column 45
[3] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
[4] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2205 - 2208
[6] Patent: US4705900, 1987, A,
[7] Patent: US4788348, 1988, A,
[8] Patent: EP2351743, 2011, A1, . Location in patent: Page/Page column 240
[9] Patent: JP2018/62475, 2018, A, . Location in patent: Paragraph 0027-0028
[10] Patent: WO2006/101434, 2006, A1, . Location in patent: Page/Page column 69; 70

2
[ 10031-82-0 ]
[ 6214-44-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium tetrahydroborate In methanol at 0 - 20℃; for 0.75 h;	NaBH ₄ (0.8 g, 21.7 mmol) was added to a stirred solution of 4-ethoxybenzaldehyde (3.0 g, 19.7 mmol) in methanol (50 ml) at 0⁰C over a period of 15 min and the reaction mixture stirred for 30 min at ambient temperature. The solvent was evaporated to obtain a residue which was dissolved in water and extracted with EtOAc twice. The combined organic extracts were washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure to afford (4-ethoxyphenyl)methanol in 82percent yield. LC/MS [M+H] 135.2. ¹H- NMR (400 MHz, CDCl₃) δ 7.266-7.286 (d, 2H, J=8.0 Hz), 6.872-6.893 (d, 2H, J=8.4Hz), 4.609 (s, 2H), 4.010-4.061 (q, 2H, J=6.8Hz), 1.396-1.430 (t, 3H, j=6.8 Hz).

Reference： [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 10, p. 1694 - 1698
[2] Patent: WO2010/127208, 2010, A1, . Location in patent: Page/Page column 62
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4861 - 4868
[4] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
[5] Journal of the Chemical Society, 1956, p. 2455,246
[6] Journal of the Chemical Society, 1954, p. 2351
[7] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2205 - 2208
[8] Patent: US5248825, 1993, A,
[9] Electrochimica Acta, 2012, vol. 59, p. 270 - 278
[10] Catalysis Today, 2015, vol. 247, p. 14 - 19
[11] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157

3
[ 1203546-07-9 ]
[ 6214-44-4 ]

Reference： [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 32, p. 4820 - 4826

4
[ 23676-09-7 ]
[ 6214-44-4 ]

Reference： [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 32, p. 4820 - 4826

5
[ 123-08-0 ]
[ 6214-44-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4861 - 4868

[ 6214-44-4 ] Synthesis Path-Downstream 1~88

1
[ 6214-44-4 ]
[ 6653-80-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 0.0833333 - 0.166667h;	Example 14 Preparation of 4-Ethoxybenzyl Chloride Thionyl chloride (10.4g, 87.7mmol) was added dropwise to a 0 C. solution of <strong>[6214-44-4]4-ethoxybenzyl alcohol</strong> (11.0 g, 72.4mmol) in dry CH2Cl2 (150 mL) with a catalytic amount of DMF (1 mL). Upon addition, reaction was allowed to stir for 5-10 minutes, while monitoring through TLC (CH2Cl2) for completion. Reaction mixture was concentrated under reduced pressure and the residue dissolved in minimal THF and then precipitated in cold H2O to yield a white precipitate. The solid was collected, taken up in CH2Cl2, dried and concentrated. The resulting oil was solidified by cooling with CO2/acetone. The compound as a white solid, which decomposes upon melting 11.3 g(92%). 1H NMR (300 MHz, CDCl3) delta=7.28 (d, 2H, J=6.6 Hz), 6.86 (d, 2H, J=6.6 Hz), 4.55 (s, 2H), 4.01 (q, 2H, J=6.9 Hz), 1.40 (t, 3H, J=6.9 Hz). 13C NMR (75 MHz, CDCl3) delta=159.0, 130.2, 129.7, 114.8, 63.7, 46.6, 15.0.
	With hydrogenchloride;	EXAMPLE 13 This Example illustrates the preparation of 4-ethoxybenzyl chloride. 4-Ethoxybenzyl alcohol (5 g) and concentrated hydrochloric acid (8.5 cm3) were vigorously stirred together for 30 minutes. The 2 phases were then allowed to separate, and the lower layer separated off, and diluted with chloroform. The organic solution was dried over anhydrous magnesium sulphate, and removal of the solvent by evaporation gave 4-ethoxybenzyl chloride (5.6 g). (This product is not stable on keeping, so was converted immediately to the phosphonium salt--see Example 12). 1 H nmr (CDCl3) ppm: 1.3 (t, 3H); 4.0 (q, 2H); 4.6 (s, 2H); 6.9 (d, 2H); and 7.3 (d, 2H).
	With hydrogenchloride;	EXAMPLE 13 This Example illustrates the preparation of 4-ethoxybenzyl chloride. 4-Ethoxybenzyl alcohol (5 g) and concentrated hydrochloric acid (8.5 cm3) were vigorously stirred together for 30 minutes. The 2 phases were then allowed to separate, and the lower layer separated off, and diluted with chloroform. The organic solution was dried over anhydrous magnesium sulphate, and removal of the solvent by evaporation gave 4-ethoxybenzyl chloride (5.6 g). (This product is not stable on keeping, so was converted immediately to the phosphonium salt--see Example 12). 1 H nmr (CDCl3) ppm: 1.3 (t,3H); 4.0 (q,2H); 4.6 (s,2H); 6.9 (d,2H); and 7.3 (d,2H).

	With thionyl chloride; In toluene; at 20℃; for 0.166667h;	Example 9 N-(1-{6-[(4-ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethyl)acetamide To a solution of p-ethoxybenzylalcohol (416 mg, 2.74 mmol) in toluene (1 mL) was added thionyl chloride (1.0 mL). The solution was stirred at room temperature for 10 min, and the solvent was evaporated. To the obtained residue were added DMF (1 mL), N-[1-(6-hydroxy-1-benzofuran-2-yl)ethyl]acetamide (200 mg, 0.913 mmol) obtained in Reference Example 27 and 60% sodium hydride (55 mg, 1.37 mmol). The reaction mixture was stirred at room temperature for 30 min, saturated brine was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=9:1 to ethyl acetate), and triturated with diethyl ether to give the title compound (155 mg, yield 48%). 1H NMR (CDCl3) delta 1.42 (t, J = 6.9 Hz, 3H), 1.55 (d, J = 7.3 Hz, 3H), 2.01 (s, 3H), 4.04 (q, J = 6.9 Hz, 2H), 5.01 (s, 2H), 5.25-5.37 (m, 1H), 5.79 (br, 1H), 6.48 (s, 1H), 6.89-6.92 (m, 3H), 7.03 (s, 1H), 7.35-7.38 (m, 3H).
7.66 g	With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; for 0.5h;Inert atmosphere; Cooling with ice;	Under an argon stream, <strong>[6214-44-4]p-Ethoxybenzyl alcohol</strong> (1) (6.509, 42.7 mmol) Of anhydrous methylene chloride (90 mL), The mixed solution of anhydrous N, N-dimethylformamide (70 L) was cooled with ice, Thionyl chloride (4.0 mL, 55.7 mmol) was added, And stirred for 30 minutes. The reaction solution was concentrated and dissolved in tetrahydrofuran (30 mL) Was added dropwise to ice water (150 mL). It was extracted twice with methylene chloride (50 mL) The obtained organic layer was dried with sodium sulfate, By concentrating under reduced pressure, To give compound 2 (7.66 g) as a pale yellow liquid.
	With thionyl chloride; In dichloromethane; at 0℃;	60% NaH (300 mg, 7.5 mmol) was added in one portion to a suspension of tert-butyl 8-[(4-methylpiperidin-1-yl)carbonyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2- carboxylate (1.58 g, 3.98 mmol) in DMF (30 mL) at room temperature under nitrogen. The mixture was stirred at room temperature for 20 min, then a solution of 4-ethoxybenzyl chloride in DMF (10 mL) (freshly prepared from <strong>[6214-44-4]4-ethoxybenzyl alcohol</strong> (1.10 g, 7.23 mmol) and SOCl2 (1.0 mL) in dichloromethane at 0C) was added at room temperature, and the reaction mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in dichloromethane and washed with water, dried over sodium sulfate. Removal of solvent gave the crude product, which was purified on silica gel (0-50% EtOAc in dichloromethane) to give the desired product (1.40 mg, 66%). MS (M+l): 532.2.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4861 - 4868
[2]Patent: US2006/88499,2006,A1 .Location in patent: Page/Page column 45
[3]Justus Liebigs Annalen der Chemie,1933,vol. 507,p. 1,9
[4]Justus Liebigs Annalen der Chemie,1933,vol. 507,p. 1,9
[5]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208
[6]Patent: US4705900,1987,A
[7]Patent: US4788348,1988,A
[8]Patent: EP2351743,2011,A1 .Location in patent: Page/Page column 240
[9]Patent: JP2018/62475,2018,A .Location in patent: Paragraph 0027-0028
[10]Patent: WO2006/101434,2006,A1 .Location in patent: Page/Page column 69; 70

2
[ 6214-44-4 ]
[ 2606-57-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With hydrogen bromide; In diethyl ether; water; at 0℃; for 0.5h;	Aq. HBr (7 ml) was added to a stirred solution of <strong>[6214-44-4](4-ethoxyphenyl)methanol</strong> (1 g, 6.57 mmol) in ether (25ml) at 0 C and the reaction mixture stirred for 30min at 0 C. The solvent was evaporated to obtain crude material which was dissolved in water and extracted with diethyl ether thrice. The total organic extracts were washed with water, dried over sodium sulfate and concentrated under vacuum to afford l-bromomethyl-4-ethoxybenzene in 64% yield.

Reference： [1]Patent: WO2010/127208,2010,A1 .Location in patent: Page/Page column 62-63
[2]Journal of the Chemical Society,1965,vol. 65,p. 1829 - 1843
[3]Natural Product Research,2011,vol. 25,p. 203 - 221

3
[ 1663-39-4 ]
[ 6214-44-4 ]
t-butyl 2-bromo-3-<(3-bromo-4-ethoxyphenyl)methoxy>propanoate [ No CAS ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 2639 - 2645

4
[ 6214-44-4 ]
[ 108-88-3 ]
1-ethoxy-4-(4-methylbenzyl)benzene [ No CAS ]
1-(4-ethoxybenzyl)-2-methylbenzene [ No CAS ]

Reference： [1]Chemical Communications,1996,p. 1517 - 1518

5
[ 6214-44-4 ]
[ 42074-68-0 ]
[ 196814-73-0 ]
(S)-2-(2-Benzoyl-phenylamino)-3-[4-(4-ethoxy-benzyloxy)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 5037 - 5054

6
[ 6214-44-4 ]
[ 221121-67-1 ]
6-(2,6-dichloro-benzyl)-2-(4-ethoxy-benzylsulfanyl)-5-methyl-3<i>H</i>-pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 8000 - 8008

7
[ 870724-38-2 ]
[ 6214-44-4 ]
[ 870724-39-3 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7750 - 7763

8
[ 6214-44-4 ]
[ 134-96-3 ]
[ 881854-95-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2060 - 2071

9
[ 6214-44-4 ]
[ 6775-77-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

10
[ 6214-44-4 ]
[ 723294-99-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

11
[ 6214-44-4 ]
3-(4-Ethoxyphenyl)-8H-thieno[2,3-b]pyrrolizin-8-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

12
[ 6214-44-4 ]
4-(4-ethoxy-phenyl)-3-pyrrol-1-yl-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

13
[ 6214-44-4 ]
Benzenesulfonic acid (Z)-2-cyano-2-(4-ethoxy-phenyl)-vinyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

14
[ 6214-44-4 ]
[4-(4-ethoxy-phenyl)-3-pyrrol-1-yl-thiophen-2-yl]-pyrrolidin-1-yl-methanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

15
[ 6214-44-4 ]
Sodium; (Z)-2-cyano-2-(4-ethoxy-phenyl)-ethenolate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

16
[ 6214-44-4 ]
(4-ethoxy-benzyl)-(4-methoxy-benzyl)-methyl-amine [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1933,vol. 507,p. 1,9

17
methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate [ No CAS ]
[ 6214-44-4 ]
methyl 2-(4-ethoxybenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate [ No CAS ]

Reference： [1]Patent: EP1182195,2002,A1 .Location in patent: Example 39

18
[ 307299-96-3 ]
[ 6214-44-4 ]
[ 307299-98-5 ]

Reference： [1]Patent: EP1182195,2002,A1 .Location in patent: Example 9

19
[ 2150-43-8 ]
[ 6214-44-4 ]
[4-3,4]2G₁COOCH₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In N,N-dimethyl-formamide;	This molecule was synthesized following the same general procedure as that for the preparation of [4-3,4]MeG1CO2CH3; K2CO3 (20.6 g, 149 mmol), methyl 3,4-dihydroxybenzoate (5.58 g, 33.2 mmol), 4-ethoxybenzyl chloride (11.3 g, 66.4 mmol), DMF (120 mL). TLC (CH2Cl2), flash column chromatography: silica gel CH2Cl2, yield: 11.45 g (79%) of the title compound as a white solid. mp 31-33 C. 1H NMR (300 MHz, CDCl3) delta=7.63 (m, 2H), 7.34 (t, 4H, J=8.7 Hz), 6.92 (d, 1H, J=8.4 Hz), 6.87 (d, 4H, J=6.6 Hz),5.10 (d, 4H, J=7.5 Hz),4.01 (q, 4H, J=6.9 Hz), 3.86 (s, 3H), 1.41 (t, 6H, J=6.9 Hz). 13C NMR (75 MHz, CDCl3) delta=167.0, 158.9, 153.2, 148.6, 129.3, 129.1, 129.0, 128.6, 124.1, 123.1, 115.9, 114.7, 113.6, 71.3, 70.9, 63.6, 52.1, 15.0.

Reference： [1]Patent: US2006/88499,2006,A1 .Location in patent: Page/Page column 47

20
[ 307299-95-2 ]
[ 6214-44-4 ]
[ 307299-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran;	Reference Example 9 To a solution of methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (300 mg), <strong>[6214-44-4]4-ethoxybenzyl alcohol</strong> (0.36 g) and triphenylphosphine (0.62 g) in THF (10 ml) was added at 0 C. diisopropyl azodicarboxylate (0.47 ml), and the resulting mixture was stirred at room temperature for 3.5 days. After concentration under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate/hexane 1:1) to obtain methyl 7-[(4-ethoxybenzyl)oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (279 mg) as colorless crystals. 1H-NMR (200 MHz, CDCl3) delta1.43 (3H, t, J=7.0 Hz), 3.03-3.10 (2H, m), 3.58-3.65 (2H, m), 3.85 (3H, s), 4.05 (2H, q, J=7.0 Hz), 5.07 (2H, s), 6.92 (2H, d, J=8.8 Hz) 7.01-7.06 (2H, m), 7.33 (2H, d, J=8.8 Hz), 7.77 (1H, s), 8.08 (1H, d, J=9.2 Hz).

Reference： [1]Patent: US6627651,2003,B1

21
[ 307300-47-6 ]
[ 6214-44-4 ]
[ 307300-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran; di-isopropyl ether;	Reference Example 39 To triphenylphosphine (590 mg, 2.25 mmol), <strong>[6214-44-4]4-ethoxybenzyl alcohol</strong> (342 mg, 2.25 mmol) and methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (327 mg, 1.50 mmol) dissolved in THF (6 ml) was added at 0 C. a solution of diisopropyl azodicarboxylate (0.439 ml, 2.23 mmol) in THF (2 ml), and the resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure and the residue was subjected to column chromatography (silica gel: 50 g, ethyl acetate/hexane=1/25?1/19). The objective fractions were concentrated under reduced pressure, diisopropyl ether was added to the residue and an insoluble material was collected by filtration. The insoluble material was washed with diisopropyl ether and was then dried under reduced pressure to obtain methyl 2-(4-ethoxybenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (308 mg, 0.87 mmol, 58%). IR (KBr): 1709 cm-1. 1H-NMR (CDCl3): delta1.42 (3H, t, J=7.0 Hz), 1.95-2.1 (2H, m), 2.55-2.8 (4H, m), 3.81 (3H, s), 4.05 (2H, q, J=7.0 Hz), 4.97 (2H, s), 6.84 (1H, dd, J=2.7, 8.3 Hz), 6.91 (2H, d, J=8.7 Hz), 6.92 (1H, d, J=2.7 Hz), 7.34 (2H, d, J=8.7 Hz), 7.65 (1H, s).

Reference： [1]Patent: US6627651,2003,B1

22
[ 6214-44-4 ]
[ 100-83-4 ]
[ 1972-28-7 ]
3-(4-ethoxybenzyloxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In tetrahydrofuran; diethyl ether;	Mix <strong>[6214-44-4]4-ethoxybenzyl alcohol</strong> (3.35 g. 22 mmol), 3-hydroxybenzaldehyde (2.69 g, 22 mmol), triphenylphosphine (5.8 g, 22 mmol) and diethylazadicarboxylate (3.83 g, 22 mmol) in tetrahydrofuran (25 mL). Stir at room temperature under anhydrous atmosphere until the reaction is done. Concentrate the solution in vacuo and dilute with a small quantity of ethyl ether. Filter any precipitate and concentrate the filtrate in vacuo. Purify by silica gel chromatography to give 3-(4-ethoxybenzyloxy)benzaldehyde.

Reference： [1]Patent: US5248825,1993,A

23
[ 6214-44-4 ]
4-[(4-ethoxyphenyl)-methyl]-1,2-dihydro-5-methyl-3H-pyrazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 5 4-[(4-Ethoxyphenyl)methyl]-1,2-dihydro-5-methyl-3 H -pyrazol-3-one The title compound was prepared in a similar manner to that described in Example 1 using <strong>[6214-44-4]4-ethoxybenzyl alcohol</strong> instead of 4-isopropoxybenzyl alcohol. 1H-NMR (500MHz, DMSO-d6) delta ppm: 1.20-1.35 (3H, m), 1.98 (3H, s), 3.46 (2H, s), 3.85-4.05 (2H, m), 6.70-6.85 (2H, m), 6.95-7.10 (2H, m)

Reference： [1]Patent: EP1213296,2002,A1

24
[ 6214-44-4 ]
[ 10031-82-0 ]

Yield	Reaction Conditions	Operation in experiment
98%Chromat.	With ammonium cerium (IV) nitrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetraethylammonium bromide; oxygen; sodium nitrite; In water; at 80℃; under 2250.23 Torr; for 2h;Autoclave; Sealed tube;	General procedure: All oxidation experiments are performed in a 120mL autoclave equipped with the magnetic stirring and temperature control. A typical procedure for the oxidation of benzyl alcohol is as follows: 1.08g (10.0mmol) of benzyl alcohol, 0.0156g (0.1mmol) of TEMPO, 0.274g (0.5mmol) of CAN, 0.0690g (1.0mmol) of NaNO2, additive in suitable amount and 10mL of H2O were charged into the reactor, and the atmosphere inside is replaced with oxygen after the reactor is sealed. Then, pure oxygen is charged to 0.3MPa at room temperature. In the following, the autoclave is heated to 80C under stirring, and then kept for 2h. After reaction, the autoclave was cooled to room temperature and excess gas was purged. The mixture was transferred into a flask, in which the reactor was washed with CH2Cl2 for 3-5 times in order to transfer completely. Next, the products are extracted with 6mL CH2Cl2 three times. The obtained products were analyzed with internal standard technique by GC with a flame ionization detector (all products were determined on GC-MS with an Agilent 6890N GC/5973 MS detector).
	With N-Bromosuccinimide; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; In dichloromethane; at 90℃; under 2250.23 Torr; for 2h;Autoclave;Catalytic behavior;	General procedure: All oxidation experiments are performed in a 120 mL autoclave equipped with the magnetic stirring and automatic temperature control. A typical procedure for the oxidation of 1 is as follows: a CH2Cl2 (10 mL) solution of 1 (1.0 g, 9.2 mmol), NBS (3.0 mol%), DDQ (7.0 mol%), and NaNO2 (10.0 mol%) is charged into the reactor, and the atmosphere inside is replaced with the pure oxygen after the reactor is sealed. Under stirring, oxygen is charged to 0.3 MPa at room temperature and the autoclave is preheated to 90 C, and then kept for 2 h. After reaction, the autoclave was cooled and the mixture is analyzed by GC and GC-MS after the excess gas (unreacted oxygen and little nitrogen oxide) is purged.

Reference： [1]Synthetic Communications,2008,vol. 38,p. 2638 - 2645
[2]Zeitschrift fur Physikalische Chemie,2011,vol. 225,p. 249 - 263
[3]Journal of Molecular Liquids,2010,vol. 155,p. 85 - 90
[4]Applied Catalysis A: General,2012,vol. 413-414,p. 332 - 339
[5]Chemical Communications,2012,vol. 48,p. 6235 - 6237
[6]Catalysis Communications,2014,vol. 43,p. 112 - 115
[7]Journal of Molecular Catalysis A: Chemical,2014,vol. 391,p. 1 - 6
[8]Inorganic Chemistry,2020,vol. 59,p. 2636 - 2640

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[ 881854-95-1 ]