Hydrochloric Acid → HCID 53847826, compound

HRID 1679909Notes

Reaction equation

HRID 1679909 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[CH:17]12[C:23](=[O:24])[O:22][C:20](=[O:21])[CH:18]1[CH2:19]2.Cl>[N+](C1C=CC=CC=1)([O-])=O>[CH:7]1([C:1]2[CH:2]=[CH:3][C:4]([C:23]([C@H:17]3[CH2:19][C@H:18]3[C:20]([OH:22])=[O:21])=[O:24])=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13229CyclohexylbenzeneHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 53847826HCID 53847826, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

14.3 g (89.2 millimoles) of cyclohexylbenzene are added dropwise to 23.7 g (0.18 mole) of anhydrous aluminum chloride in 50 ml of nitrobenzene at 10°-15° C., whilst stirring. 10.0 g (89.2 millimoles) of 1,2-cyclopropanedicarboxylic acid anhydride are then added, a little at a time, at the same temperature and thereafter the mixture is stirred for 20 hours at room temperature, followed by 1 hour at 50° C. The solution is introduced into a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid. The nitrobenzene is removed by steam distillation and the solid which has precipitated is filtered off at 10° C. and dissolved in aqueous sodium carbonate solution. The solution is filtered and the filtrate is acidified with concentrated hydrochloric acid. The solid which precipitates is filtered off, washed with water and dried under reduced pressure at 50° C. 19.9 g (82% of theory) of cis-2-(p-cyclohexylbenzoyl)-cyclopropanecarboxylic acid are obtained as almost colorless crystals of melting point 162°-163° C. after recrystallization from methanol.

Workup

  1. stirringa little at a time, at the same temperature and thereafter the mixture is stirred for 20 hours at room temperature
  2. customThe nitrobenzene is removed by steam distillation
  3. customthe solid which has precipitated
  4. filtrationis filtered off at 10° C.
  5. dissolutiondissolved in aqueous sodium carbonate solution
  6. filtrationThe solution is filtered
  7. customThe solid which precipitates
  8. filtrationis filtered off
  9. washwashed with water
  10. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-6784d37229ff4d72aa37e61b321bcc5f
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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