Methanol → Methyl 2-(4-chlorophenyl)-2-hydroxyacetate

HRID 2177052Notes

Reaction equation

HRID 2177052 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:8][C:7](=[O:9])[CH:6]([C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1)[OH:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 102994-Chloromandelic acid

Product 1

HCID 13794067Methyl 2-(4-chlorophenyl)-2-hydroxyacetate

Procedure

To a stirred solution of 4-chloromandelic acid (10.0 g, 53.6 mmol) in methanol was added sulfuric acid (3.1 mL, 58.9 mmol). The reaction mixture was refluxed for 6 hours. The reaction mixture was concentrated, neutralized with sat. sodium carbonate solution, extracted with ether, washed with brine, dried, and concentrated. Purification by silica gel chromatography (40% ethyl acetate in hexanes) yielded 10.0 g of (4-chlorophenyl)hydroxyacetic acid methyl ester.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ether
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d6dd360bcafb44d7a17abd7da7765562
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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