Toluene → HCID 53822285, compound

HRID 1679907Notes

Reaction equation

HRID 1679907 reaction equation
CN(C)C=O.[Cl-].[Al+3].[Cl-].[Cl-].[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:17]12[C:23](=[O:24])[O:22][C:20](=[O:21])[CH:18]1[CH2:19]2>>[C:10]1([CH3:16])[CH:15]=[CH:14][C:13]([C:23]([C@H:17]2[CH2:19][C@H:18]2[C:20]([OH:22])=[O:21])=[O:24])=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 53822285HCID 53822285, compoundYield 90%

Conditions

Temperature
70 °C

Procedure

18 ml (0.23 mole) of dimethylformamide are added dropwise in the course of a few minutes, whilst stirring, to 120 g (0.90 mole) of anhydrous aluminum chloride, resulting in a strongly exothermic reaction. 8.2 g (89.0 millimoles) of toluene are then added dropwise at 60°-70° C. Thereafter, 10.0 g (89.2 millimoles) of 1,2-cyclopropanedicarboxylic acid anhydride are added, a little at a time, at the same temperature, and the mixture is stirred for a further hour at 70° C. The melt is then introduced into 1 kg of ice. The solid which has precipitated is filtered off, washed with water and dried under reduced pressure at 50° C. 16.3 g (90% of theory) of cis-2-(p-toluoyl)-cyclopropanecarboxylic acid are obtained as colorless crystals, of melting point 165°-166° C. after recrystallization from ethyl acetate.

Workup

  1. customresulting in a strongly exothermic reaction
  2. customThe solid which has precipitated
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-a753bfaf500e4213a906e53cd1adf36a
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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