4-Chlorobenzoyl chloride → 3,3-Dimethyl-4-(4'-chloro-phenacyl)-gamma-butyrolactone

HRID 2295482Notes

Reaction equation

HRID 2295482 reaction equation
C[O:2][C:3](=[O:10])[CH2:4][C:5]([CH3:9])([CH3:8])[CH:6]=[CH2:7].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH3:9][C:5]1([CH3:8])[CH:6]([CH2:7][C:16]([C:15]2[CH:19]=[CH:20][C:12]([Cl:11])=[CH:13][CH:14]=2)=[O:17])[O:2][C:3](=[O:10])[CH2:4]1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 24287Tin tetrachlorideHCID 114129Methyl 3,3-dimethyl-4-pentenoate

Product 1

HCID 204745093,3-Dimethyl-4-(4'-chloro-phenacyl)-gamma-butyrolactone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

71 g (0.5 mol) of 3,3-dimethyl-4-pentenoic acid methyl ester were added dropwise to a mixture of 87.5 g (0.5 mol) of p-chlorobenzoyl chloride and 130.3 g (0.5 mol) of tin tetrachloride at 20° C., while cooling with ice. After being left to stand overnight, the reaction mixture had solidified. It was taken up in methylene chloride, the methylene chloride mixture was filtered and the filtrate was extracted by shaking with dilute hydrochloric acid. After drying and stripping off the solvent in vacuo, 111.1 g of crude product (about 83%), which crystallized completely, were obtained. Recrystallization from 120 ml of ethanol gave 3,3-dimethyl-4-(4'-chloro-phenacyl)-γ-butyrolactone of melting point 76°-80° C.

Workup

  1. temperaturewhile cooling with ice
  2. waitAfter being left
  3. filtrationthe methylene chloride mixture was filtered
  4. extractionthe filtrate was extracted
  5. customAfter drying
  6. customcrystallized completely
  7. customwere obtained
  8. customRecrystallization from 120 ml of ethanol

Sources & evidence

ORD record
ord-7d7827893e914ba58ff66a8dbda3cf22
Source dataset
uspto-grants-1984_01
Patent number
US04425282

Reaction notes

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