Acetophenone → Phenylpyruvic acid

HRID 1789595Notes

Reaction equation

HRID 1789595 reaction equation
[OH-:1].[Ca+2].[OH-:3].[CH2:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[CH3:13]>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2].O>[C:5]1([CH2:4][C:15](=[O:3])[C:12]([OH:14])=[O:1])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:15]1([CH2:12][C:13]([OH:3])=[O:1])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 7410AcetophenoneHCID 7503Benzyl ChlorideHCID 6093208Calcium Hydroxide

Product 2

HCID 997Phenylpyruvic acidHCID 999Phenylacetic Acid

Reagents, catalysts & solvents 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)CatalystHCID 962WaterSolvent

Procedure

Into a stainless steel-made autoclave of 135 ml capacity were introduced 25 ml of water, 4.7 g of calcium hydroxide, 3.8 g of benzyl chloride and 50 ml of the organic solution of acetophenone containing the cobalt carbonyl catalyst and recovered in Example 6 to form a reaction mixture. The reaction and subsequent processing of the reaction mixture were performed in substantially the same manner as in Example 6. The yields of phenyl pyruvic acid and phenyl acetic acid were 71.5% and 22.0%, respectively, of the respective theoretical values based on the amount of benzyl chloride.

Workup

  1. customrecovered in Example 6
  2. customto form a reaction mixture
  3. customThe reaction and subsequent processing of the reaction mixture

Sources & evidence

ORD record
ord-153ada47a0d1474199f382bca6a97f00
Source dataset
uspto-grants-1987_08
Patent number
US04689431

Reaction notes

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