Chloroacetone → HCID 22022034, compound

HRID 1793299Notes

Reaction equation

HRID 1793299 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.Cl[CH2:14][C:15](=O)[CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10](=[O:12])[O:11][CH2:14][C:15]=2[CH3:16])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 15719(3-Methoxyphenyl)acetic acid

Product 1

HCID 22022034HCID 22022034, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-methoxyphenylacetic acid (3.32 g, 20 mmol), chloroacetone (2.02 g, 22 mmol) and potassium carbonate (6.07 g, 44 mmol) in acetonitrile (30 mL) was heated at reflux for 5 hours. The resultant mixture was cooled to room temperature, diluted with ethyl acetate (60 ml), filtered through a silica gel pad, and washed with ethyl acetate (2×50 mL). The filtrate was concentrated in vacuo and the residue was treated with ether and hexanes to give a yellowish solid (3.2 g, 78% yield). 1H NMR (CDCl3):2.22 (s, 3H), 3.84 (s, 3H), 4.79 (s, 2H), 6.92 (m, 1H), 7.05 (m, 2H), 7.36 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. filtrationfiltered through a silica gel pad
  4. washwashed with ethyl acetate (2×50 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionthe residue was treated with ether and hexanes

Sources & evidence

ORD record
ord-d90d6fe554fe4673b93da7fd41450434
Source dataset
uspto-grants-2006_07
Patent number
US07081459B2

Reaction notes

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