Hydrochloric Acid → Ethyl 4-(4-chlorophenyl)-4-oxobut-2-enoate

HRID 638519Notes

Reaction equation

HRID 638519 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:10])/[CH:5]=[CH:6]/[C:7](O)=[O:8].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[CH2:23](Cl)Cl>>[CH2:2]([O:3][C:4](=[O:10])[CH:5]=[CH:6][C:7]([C:15]1[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=1)=[O:8])[CH3:23]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 86740569HCID 86740569, compound

Product 1

HCID 54524585Ethyl 4-(4-chlorophenyl)-4-oxobut-2-enoate

Conditions

Temperature
40 °C

Procedure

Fifteen grams (92 m mol) of fumaric acid monomethyl ester chloride were added dropwise under stirring over a period of 25 minutes to a mixture of 200 ml of chlorobenzene and 18.4 gm (138 m mol) of aluminum chloride at 20° C. After heating for 45 minutes at 40° C., the mixture was cooled, poured on ice/water containing 30 ml of concentrated hydrochloric acid, and taken up in methylene chloride, and the solution was evaporated (under reduced pressure toward the end). The residue was recrystallized from petroleum ether, and 5.7 gm of pure 4-(4'-chlorophenyl)-4-oxo-but-2-enoic acid ethyl ester (melting point: 58°-60° C.) were obtained.

Workup

  1. temperaturethe mixture was cooled
  2. customthe solution was evaporated (under reduced pressure toward the end)
  3. customThe residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-74647cc4537d4c3aa4da2b26f07c5f60
Source dataset
uspto-grants-1985_12
Patent number
US04562068

Reaction notes

Loading…