Hydrochloric Acid → 3,4-Dimethyl-2-pentenoylchloride

HRID 1702963Notes

Reaction equation

HRID 1702963 reaction equation
[CH3:1][C:2]([CH:9]([CH3:11])[CH3:10])=[CH:3][C:4](OCC)=[O:5].S(Cl)([Cl:14])=O.Cl>C1C=CC=CC=1>[CH3:1][C:2]([CH:9]([CH3:11])[CH3:10])=[CH:3][C:4]([Cl:14])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 281491Ethyl 3,4-dimethyl-2-pentenoate

Product 1

HCID 541273923,4-Dimethyl-2-pentenoylchloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,4-Dimethyl-2-pentenoic acid (XI, 4.1 g) was heated to a gentle boil with thionyl chloride (50 g) in benzene (50 mL) until the generation of hydrochloric acid gas ceased. Removal of the excess thionyl chloride and benzene by evaporation in vacuo followed by a distillation of the reaction product gave pure 3,4-dimethyl-2-pentenoylchloride (IX, 64° C. (9.5 mm)).

Workup

  1. customRemoval of the excess thionyl chloride and benzene
  2. customby evaporation in vacuo
  3. distillationfollowed by a distillation of the reaction product

Sources & evidence

ORD record
ord-ca025f933d654ceab519a593a8a60d57
Source dataset
uspto-grants-1982_09
Patent number
US04350638

Reaction notes

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