Hydrochloric Acid → HCID 178468152, compound

HRID 1981248Notes

Reaction equation

HRID 1981248 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:12](Cl)(=[O:14])[CH3:13].[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1.Cl>C(O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:16]2[CH2:21][CH2:20][C@H:19]([C:12](=[O:14])[CH3:13])[CH2:18][CH2:17]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 6367Acetyl chlorideHCID 7964ChlorobenzeneHCID 8079CyclohexeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178468152HCID 178468152, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

To a mixture of chlorobenzene (1500 g, 13.3 moles) and aluminum chloride (1080 g, 8.1 moles), a mixture of acetyl chloride (473 g, 6.0 moles) and cyclohexene (555 g, 6.8 moles) was dropwise added in about 3 hours while maintaining the temperature at a level of not higher than -20° C. After the dropwise addition, the reaction system was brought to room temperature. After the termination of the generation of hydrogen chloride gas, the reaction mixture was poured into 5 l of 1:1 hydrochloric acid. After separating the organic layer, the aqueous layer was extracted with diethyl ether, and the organic layers thereby obtained were put together and then dried. The solvent was distilled off by an evaporator. The remaining oily substance was distilled under reduced pressure, whereby 1131 g of a fraction having a boiling point of from 120° to 130° C./0.1 mmHg was obtained. To this fraction, 2 l of a 1:1 mixture of methanol and ethanol was added, and the mixture was cooled in a dry ice/methanol bath to obtain crude crystals. The crude crystals were recrystallized from 500 ml of methanol, whereby 165 g of trans-4-(p-chlorophenyl)-1-acetyl-cyclohexane was obtained. The yield was 12%, and the melting point was 74.6° C.

Workup

  1. additionwas dropwise added in about 3 hours
  2. additionAfter the dropwise addition
  3. customwas brought to room temperature
  4. customAfter separating the organic layer
  5. extractionthe aqueous layer was extracted with diethyl ether
  6. customthe organic layers thereby obtained
  7. customdried
  8. distillationThe solvent was distilled off by an evaporator
  9. distillationThe remaining oily substance was distilled under reduced pressure, whereby 1131 g of a fraction
  10. customof from 120° to 130° C./0.1 mmHg
  11. customwas obtained
  12. additionwas added
  13. temperaturethe mixture was cooled in a dry ice/methanol bath
  14. customto obtain crude crystals
  15. customThe crude crystals were recrystallized from 500 ml of methanol

Sources & evidence

ORD record
ord-2cec3bc8fc4f469b9c97fd1e25e3c561
Source dataset
uspto-grants-1985_04
Patent number
US04514044

Reaction notes

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