Sulfuric Acid → Ethyl alpha-oxobenzenebutanoate

HRID 892634Notes

Reaction equation

HRID 892634 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([OH:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].Cl[O-].[Na+].S(=O)(=O)(O)O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[C:5](=[O:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4092621Ethyl 2-hydroxy-4-phenylbutyrate, (+-)-HCID 23665760Sodium Hypochlorite

Product 1

HCID 562087Ethyl alpha-oxobenzenebutanoateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the same procedure as described in Example 2, using 20.8 g (100 mmol) of 2-hydroxy-4-phenylbutyric acid ethyl ester, methylene chloride (50 ml), 72.6 g (purity 12.3%, 120 mmol) of sodium hypochlorite, 43 mg (0.2 mmol) of 4-acetoxy-2,2,6,6-tetramethylpiperidinyl-1-oxy, and 10 ml (10 mmol) of 1N sulfuric acid, was obtained 18.95 g of 2-keto-4-phenylbutyric acid ethyl ester. The yield was 92%.

Sources & evidence

ORD record
ord-abedc3d8d2fa437a8010cdd2ded2491d
Source dataset
uspto-grants-1992_06
Patent number
US05118833

Reaction notes

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