Toluene → HCID 57591519, compound

HRID 1784151Notes

Reaction equation

HRID 1784151 reaction equation
Cl[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[CH:3]=1.[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>ClCCl.[Cl-].[Cl-].[Zn+2]>[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([O:18][C:2]2[CH:8]3[CH2:9][CH:5]([CH2:6][CH2:7]3)[C:4](=[O:10])[CH:3]=2)=[O:17])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 63184-Chlorobenzoic AcidHCID 81531DiisopropylethylamineHCID 57591516HCID 57591516, compound

Product 1

HCID 57591519HCID 57591519, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 500 mg of 4-chlorobicyclo[3.2.1]oct-3-en-2-one (Preparation Example P2), 440 mg of ZnCl2, 400 mg of 4-chlorobenzoic acid, 1.05 g of diisopropylethylamine and 5 ml of toluene is stirred at room temperature under a nitrogen atmosphere at reflux temperature for 6 hours. After cooling, the reaction mixture is then diluted with dichloromethane and washed with 5% aqueous sulfuric acid and 5% aqueous sodium hydroxide. After concentration of the organic phase to dryness by evaporation, 0.6 g of 4-(4-chlorophenyl-carbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one is obtained.

Workup

  1. temperatureat reflux temperature for 6 hours
  2. temperatureAfter cooling
  3. washwashed with 5% aqueous sulfuric acid and 5% aqueous sodium hydroxide
  4. customAfter concentration of the organic phase to dryness by evaporation

Sources & evidence

ORD record
ord-409d008ed9254c7a90cc86e77c706786
Source dataset
uspto-grants-2009_03
Patent number
US07501544B2

Reaction notes

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