Hydrochloric Acid → 4-Phenyl-cyclohexanecarboxylic acid

HRID 427410

Reaction equation

HRID 427410 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([C:11]([OH:13])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=1.Cl>C1C=CC=CC=1>[C:5]1([CH:8]2[CH2:9][CH2:10][CH:5]([C:11]([OH:13])=[O:12])[CH2:6][CH2:7]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 694701-Cyclohexene-1-carboxylic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3448124-Phenyl-cyclohexanecarboxylic acidYield 76.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of AlCl3 (13 g, 97.5 mmol, 1.0 equiv) in benzene (100 mL) kept at 35° C., was added 1-cyclohexenecarboxylic acid (5 g, 39.7 mmol, 0.41 equiv) dropwise. After addition was complete, the reaction solution was heated to 70° C. for 1 h and 45° C. overnight. The reaction was cooled, and 200 mL of 1 N HCl was slowly added. The product was extracted with EtOAc. The organic layer was extracted with 1 N NaOH and the aqueous layer was acidified with concentrated HCl to produce a white precipitate that was collected by filtration, washed with water and dried to give the titled compound as a white solid (3.1 g, 38%) which was used without further purification.

Workup

  1. customkept at 35° C.
  2. additionAfter addition
  3. temperatureThe reaction was cooled
  4. extractionThe product was extracted with EtOAc
  5. extractionThe organic layer was extracted with 1 N NaOH
  6. customto produce a white precipitate that
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-9304d89c4e324764996841c307a765a8
Source dataset
uspto-grants-2001_11
Patent number
US06313117B1

Linked notes

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