1-Octanethiol → Ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoate

HRID 2422246Notes

Reaction equation

HRID 2422246 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCCCCCC>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 81441-OctanethiolHCID 6451240Aluminum(III) ChlorideHCID 23082987Ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate

Product 1

HCID 23082713Ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution (20 ml) of ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate (1.17 g, 4.79 mmol), aluminum chloride (1.9 g, 14.2 mmol) and 1-octanethiol (1.7 ml, 9.80 mmol) in dichloromethane was stirred from ice-cooling to room temperature for 4 hrs. The reaction solution was poured into ice water, and the mixture was stirred for 1 hr. The mixed solution was extracted with dichloromethane, and the extract was washed with aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.0 g) as a colorless oil. yield 91%. MS 230.9 (MH+).

Workup

  1. extractionThe mixed solution was extracted with dichloromethane
  2. washthe extract was washed with aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6771bde20d5b43b7b9eb7a7e711cee50
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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