Hydrochloric Acid → 3-Chloro-4-cyclohexylcinnamic acid

HRID 2419405Notes

Reaction equation

HRID 2419405 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-e5bf84aa5d564ebc9371dcfc6d090b65
Source dataset
uspto-grants-1978_08
Patent number
US04105786

Reaction notes

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