Phenylacetonitrile → Diethyl 4-cyano-4-phenylheptanedioate

HRID 1287851Notes

Reaction equation

HRID 1287851 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12]>>[C:8]([C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:12][CH2:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])[CH2:12][CH2:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])#[N:9]

Participants

3

Reactant 2

HCID 8794PhenylacetonitrileHCID 8821Ethyl Acrylate

Product 1

HCID 13286928Diethyl 4-cyano-4-phenylheptanedioate

Procedure

The required diethyl γ-cyano-γ-phenylpimelate was prepared by reacting phenylacetonitrile with ethyl acrylate according to the general method of Koelsch, J. Am. Chem. Soc., 65, 437 (1943). This product, boiling point 148°-151° C. at 0.04 mm [Branchini et al., Ann. Chim. (Rome) 51, 1382 (1961) report 170°-172° C. at 0.2 mm] was obtained in addition to the mono-Michael addition product reported by Koelsch.

Workup

  1. customThis product, boiling point 148°-151° C. at 0.04 mm [Branchini et al., Ann. Chim. (Rome) 51, 1382 (1961) report 170°-172° C. at 0.2 mm] was obtained in addition to the mono-Michael addition product

Sources & evidence

ORD record
ord-cae515eef497451aa664cdbe59ba85a2
Source dataset
uspto-grants-1976_10
Patent number
US03985888

Reaction notes

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