Hydrochloric Acid → HCID 54457144, compound

HRID 1282833Notes

Reaction equation

HRID 1282833 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[Cl:8][C:9]1(Cl)[CH2:11][C:10]1([CH3:13])[CH3:12].Cl>>[Cl:8][C:9]1[CH2:11][CH:2]2[C:1]([O:6][C:4](=[O:5])[CH:3]2[CH2:12][C:10]=1[CH3:13])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 522349HCID 522349, compound

Product 1

HCID 54457144HCID 54457144, compoundYield 13.6%

Procedure

To a glass tube was added maleic anhydride (73.3 mg., 0.75 mmole) and 1,1-dichloro-2,2-dimethylcyclopropane (119.3 mg., 0.86 mmole). The tube was sealed and heated at 165°-170°C. for 6-8 hours. The tube was allowed to cool and was opened (caution HCl pressure). The initially liquid product mixture crystallized with vigorous evolution of hydrogen chloride. Extraction of the crude solid (m.p. 60°-70°C.) with boiling n-hexane gave 1-chloro-2-methylcyclohexene-4,5-dicarboxylic anhydride (20.5 mg., 10 percent yield, white plates m.p. 76°-78°C.). The melting point of 1-chloro-2-methylcyclohexene-4,5-dicarboxylic anhydride as reported in the literature, J. Applied Chem. (London) 3, 145 (1953), is 79°-80°C.

Workup

  1. customThe tube was sealed
  2. temperatureheated at 165°-170°C. for 6-8 hours
  3. temperatureto cool
  4. customThe initially liquid product mixture crystallized with vigorous evolution of hydrogen chloride
  5. extractionExtraction of the crude solid (m.p. 60°-70°C.) with boiling n-hexane

Sources & evidence

ORD record
ord-483d92459cc44f7dad28b3ced3050151
Source dataset
uspto-grants-1976_08
Patent number
US03972901

Reaction notes

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