Hydrochloric Acid → HCID 20544225, compound

HRID 2285758Notes

Reaction equation

HRID 2285758 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)C(O)=O)C.[OH-].[K+].Cl>O.C(O)C>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:5][C:4]([OH:21])=[O:3])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 53916502HCID 53916502, compound

Product 1

HCID 20544225HCID 20544225, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

80 g of 5-(4-chlorophenyl)pentylmalonic acid ethyl ester are boiled under reflux with 45 g of potassium hydroxide in 230 ml of water and 100 ml of ethanol for 5 hours; after cooling, the mixture is adjusted to pH 1-2 with concentrated hydrochloric acid and is extracted 3 times with diethyl ether. The combined organic solutions are concentrated and the residue [5-(4-chlorophenyl)pentylmalonic acid] is heated to 160° for 3.5 hours. The residue consists of 51 g of 7-(4-chlorophenyl)heptanoic acid of m.p. 75° to 78°.

Workup

  1. temperatureafter cooling
  2. extractionis extracted 3 times with diethyl ether
  3. concentrationThe combined organic solutions are concentrated
  4. temperaturethe residue [5-(4-chlorophenyl)pentylmalonic acid] is heated to 160° for 3.5 hours

Sources & evidence

ORD record
ord-3843d67fdf8440fbac94a55589e351d6
Source dataset
uspto-grants-1982_04
Patent number
US04324796

Reaction notes

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