Ethyl butyrate → Ethyl 3-phenylprop-2-enoate

HRID 1156448Notes

Reaction equation

HRID 1156448 reaction equation
O1[CH2:6][CH2:5]OCC1.[C:7]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:8][CH2:9][CH3:10].[C:15](#N)[CH2:16][CH3:17].C(=O)(OCC)OCC>C1(C)C=CC=CC=1.CN(C)C=O.C(O)(C)(C)C.C1CCCCC1.ClC1C=CC=CC=1>[C:7]([O:12][CH2:13][CH3:14])(=[O:11])[CH:8]=[CH:9][C:10]1[CH:6]=[CH:5][CH:17]=[CH:16][CH:15]=1

Participants

10

Reactant 4

HCID 7762Ethyl butyrateHCID 7766Diethyl CarbonateHCID 7854PropionitrileHCID 312751,4-Dioxane

Product 1

HCID 7649Ethyl 3-phenylprop-2-enoate

Reagents, catalysts & solvents 5

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolventHCID 7964ChlorobenzeneSolventHCID 8078CyclohexaneSolvent

Procedure

The procedure described in Example 1 is repeated, except that (a) 50 ml of dioxane, (b) 50 ml of ethyl butyrate, (c) 50 ml of propionitrile, (d) 50 ml of diethyl carbonate, (e) 50 ml of chlorobenzene, (f) 50 ml of cyclohexane, (g) 50 ml of tert.-butanol or (h) 50 ml of N,N-dimethylformamide are used in place of 50 ml of toluene. After working up as described in Example 1, ethyl cinnamate is obtained in comparably good yields.

Sources & evidence

ORD record
ord-f677d2e173534c69bf65401ab2527651
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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