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

HRID 2110844Notes

Reaction equation

HRID 2110844 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 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 (20 mL) was stirred for 4 hr while raising the temperature from under ice-cooling to room temperature. The reaction mixture was poured into ice water, and the mixture was stirred for 1 hr. The mixture was extracted with dichloromethane. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.0 g, yield 91%) as a colorless oil. MS: m/z 231 (MH+).

Workup

  1. temperaturewhile raising the temperature from under ice-
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe extract washed with aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eda0074ee88a4a35a5b611594fe9a6fc
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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