Phenylpyruvic acid → HCID 15024007, compound

HRID 1086355Notes

Reaction equation

[C:1]1([CH2:7][C:8](=[O:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]([CH2:16]Cl)=[CH2:15].[OH-].[Na+]>>[O:12]=[C:8]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:16][C:14]([Cl:13])=[CH2:15])[C:9]([OH:11])=[O:10]

Participants

Reactant 3

HCID 997Phenylpyruvic acid

HCID 65652,3-Dichloropropene

HCID 14798Sodium Hydroxide

Product 1

HCID 15024007HCID 15024007, compound

Procedure

By the same operation as in Example 45, 1.64 g (10 mmoles) of phenylpyruvic acid was reacted with 0.11 g (10 mmoles) of 2,3-dichloropropene in a 1N aqueous solution of sodium hydroxide (20 ml, 20 mmoles) to give 2-oxo-3-phenyl-5-chloro-5-hexenoic acid as a pale yellowish white solid. It was converted to a methyl ester by using diazomethane, and then the methyl ester was purified by silica gel column chromatography. Methyl 2-oxo-3-phenyl-5-chloro-5-hexenoate as a pure product (1.87 g; yield 74 %) was obtained.

Sources & evidence

ORD record: ord-957fb0ab52f64f229b7f7e1ce0c8bc6c
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05028738

Reaction notes

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