Hydrochloric Acid → 3-Chloro-4-cyclohexylcinnamic acid

HRID 616750Notes

Reaction equation

HRID 616750 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH:5]=O.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH:5]=[CH:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic Acid2×HCID 8082PiperidineHCID 107277773-Chloro-4-cyclohexylbenzaldehyde

Product 1

HCID 542933553-Chloro-4-cyclohexylcinnamic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Chloro-4-cyclohexylbenzaldehyde (0.1 mole), malonic acid (0.2 moles), and dry pyridine (175 ml) are placed in a 1 l roundbottom flask. The malonic acid is dissolved by shaking on a steam bath and piperidine (0.5 ml) is added. The reaction is allowed to take place on the steam bath for 4 hours. After standing at room temperature overnight, the mixture is refluxed for 1 hour and cooled. The reaction mixture is poured into 250 ml of ice water and acidified with concentrated hydrochloric acid (80 ml) with stirring. The crystals of product are collected by filtration, washed with water (4 × 150 ml) and air dreid. Recrystallization from acetone-water gives 3-chloro-4-cyclohexylcinnamic acid.

Workup

  1. customfor 4 hours
  2. temperaturethe mixture is refluxed for 1 hour
  3. temperaturecooled
  4. stirringwith stirring
  5. filtrationThe crystals of product are collected by filtration
  6. washwashed with water (4 × 150 ml) and air dreid
  7. customRecrystallization from acetone-water

Sources & evidence

ORD record
ord-4b5f2a3ecc334d10bf32636f214afacb
Source dataset
uspto-grants-1978_02
Patent number
US04075354

Reaction notes

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