Diethyl Oxalate → Diethyl 2-oxo-3-phenylsuccinate

HRID 1635683Notes

Reaction equation

HRID 1635683 reaction equation
C(OCC)(=O)C(C1C=CC=CC=1)=C.C(OC)(=O)C(C1C=CC=CC=1)=C.[C:26]1([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:38](OCC)(=[O:44])[C:39]([O:41][CH2:42][CH3:43])=[O:40].C([O-])C.[Na+]>>[O:44]=[C:38]([CH:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:39]([O:41][CH2:42][CH3:43])=[O:40]

Participants

6

Reactant 5

HCID 7268Diethyl OxalateHCID 7590Ethyl phenylacetateHCID 89651Ethyl 2-phenylacrylateHCID 193334Methyl atropateHCID 2723922Sodium ethoxide

Product 1

HCID 230432Diethyl 2-oxo-3-phenylsuccinate

Procedure

Ethyl atropate with a methyl atropate content not exceeding 0.05% can be obtained in a relatively complicated, two-stage process (Helv. Chim. Acta 30, 1349 (1947)) as long as the starting materials do not contain more than 0.05% of methyl compounds. This process involves ethyl phenylacetate being condensed with diethyl oxalate in the presence of sodium ethanolate to give diethyl 2-oxo-3-phenylsuccinate, Na salt. Subsequent reaction with formaldehyde in the presence of potassium carbonate results in ethyl atropate with a methyl ester content not exceeding 0.05%.

Workup

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Sources & evidence

ORD record
ord-d461cd2bd5fb4a1da12f287d1d0e73a7
Source dataset
uspto-grants-2003_01
Patent number
US06509493B1

Reaction notes

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