2-(4-Methoxyphenylthio)benzoic acid → {2-[(4-Methoxyphenyl)sulfanyl]phenyl}methanol

HRID 380351

反応式

HRID 380351 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](O)=[O:13])=[CH:5][CH:4]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[CH2:12][OH:13])=[CH:7][CH:8]=1

参加物

3

反応物 2

HCID 28248782-(4-Methoxyphenylthio)benzoic acidHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

生成物 1

HCID 818003{2-[(4-Methoxyphenyl)sulfanyl]phenyl}methanol収率 84.7%

実験手順

2-(4-Methoxyphenylsulfanyl)benzoic acid was reduced with sodium bis-(methoxyethoxy)-aluminum hydride to provide in 84.7% yield 2-(4-methoxyphenylsulfanyl)benzyl alcohol. This compound was without purification treated with thionyl chloride to provide in 95.0% yield 2-(4-methoxyphenylsulfanyl)benzyl chloride, m.p. 76-78° C. For C14H13ClOS (264.8) calculated: 63.51% C, 4.95% H, 13.39% Cl, 12.11% S; found: 63.43% C, 5.05% H, 13.16% Cl, 12.10% S. This compound was treated with sodium cyanide to provide in 94.6% yield 2-(4-methoxyphenylsulfanyl)phenylacetonitrile, m.p. 65-67° C. Alkaline hydrolysis of this nitrile provided after work-up 69.7% yield of 2-(4-methoxyphenyl-sulfanyl)phenylacetic acid, m.p. 177-179° C. Demethylation with pyridine hydrochloride provided in 82.5% yield 2-(4-hydroxyphenylsulfanyl)phenylacetic acid, m.p. 163-165° C. This acid was esterified with methanol in the presence of sulfuric acid to give the required ester in 77.8% yield, m.p. 126-128° C. For C15H14O3S (274.3) calculated: 65.69% C, 5.15% H, 11.67% S; found: 65.17% C, 5.14% H, 11.69% S. 1H NMR spectrum (CDCl3): H(O) 5.17 bs; CH2 3.85 s; aromatic H on the phenolic nucleus: H(3,5) 6.73 d, J=8.8 Hz.

出典と根拠

ORDレコード
ord-7182608fa8104a7594683e1eb2bd1965
出典データセット
uspto-grants-2001_10
特許番号
US06303612B1

関連ノート

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