Methanol → 2-(4-Methylsulfanylphenyl)ethanol

HRID 1595532Notes

Reaction equation

HRID 1595532 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[CH:5][CH:4]=1.CO>O1CCCC1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 49839124-(Methylthio)phenylacetic acid

Product 1

HCID 27600862-(4-Methylsulfanylphenyl)ethanolYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.5 ml 1 M borane-tetrahydrofuiran complex was slowly added to a solution of 1 g (5.5 mmole) 4-(methylmercapto)phenyl acetic acid in 5 ml tetrahydrofuran at −10° C. The reaction mixture was allowed to reach room temperature and the reaction was followed by TLC. After completion 10 ml methanol was added and the solvents were evaporated. Diethyl ether and 2 M sodium hydroxide was added, the phases were separated, the organic phase was dried, filtered and evaporated in vacuo to give 0.8 g (yield 84.4%) of 2-[4-(methylmercapto)phenyl]-1-ethanol.

Workup

  1. customto reach room temperature
  2. customthe solvents were evaporated
  3. additionDiethyl ether and 2 M sodium hydroxide was added
  4. customthe phases were separated
  5. customthe organic phase was dried
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-353e9ef6816b4c148bc6c84bd2d7614d
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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