Chloroform → (3,4-Dimethoxyphenyl)acetyl chloride

HRID 1418883Notes

Reaction equation

HRID 1418883 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(Cl)(Cl)[Cl:16]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([Cl:16])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 6212Chloroform2×HCID 7139(3,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Procedure

(3,4-dimethoxyphenyl)acetyl chloride is prepared according to the method described in Example 8 using 3,4-dimethoxyphenylacetic acid (2.85 g, 14.5 mmol) to give a brown oil which is dissolved in chloroform (10 mL). This solution is refluxed for 3 hours with a solution of (±)-trans-[2-(4-morpholinyl)]cyclohexanethiol (2.8 g, 14 mmol) in chloroform (10 mL) under nitrogen. The reaction mixture is partitioned between 1M sodium hydroxide solution (100 mL) and dichloromethane (80 mL). The organic layer is separated and the aqueous is washed with more dichloromethane (2×50 mL). The combined dichloromethane extracts are dried over sodium sulfate, and the solvent is removed to leave the crude free ester. This is purified by column chromatography and converted to the hydrochloride salt by treatment with HCl in ether. The product is recrystallised from hot ethyl acetate/methanol to yield the title compound.

Workup

  1. customto give a brown oil which
  2. customThe reaction mixture is partitioned between 1M sodium hydroxide solution (100 mL) and dichloromethane (80 mL)
  3. customThe organic layer is separated
  4. washthe aqueous is washed with more dichloromethane (2×50 mL)
  5. dry with materialThe combined dichloromethane extracts are dried over sodium sulfate
  6. customthe solvent is removed
  7. customto leave the crude free ester

Sources & evidence

ORD record
ord-909c1ba1f8144300933620caefe7b126
Source dataset
uspto-grants-1999_03
Patent number
US05885984

Reaction notes

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