Potassium Hydroxide → HCID 53642612, compound

HRID 1156842Notes

Reaction equation

HRID 1156842 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:24])[CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:24])[CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 540923914-Phenoxybutylmalonic acid diethyl ester

Product 1

HCID 53642612HCID 53642612, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 16.1 g of potassium hydroxide in 250 ml of ethanol is added dropwise to 87 g of 4-phenoxybutylmalonic acid diethyl ester in 250 ml of ethanol at room temperature. The mixture is stirred for 24 hours and substantially concentrated in vacuo; the residue is taken up in 500 ml of water and the aqueous mixture is extracted with 200 ml of diethyl ether. The aqueous phase is acidified with concentrated hydrochloric acid, while cooling with ice, and extracted 3 times with 200 ml of diethyl ether each time. After drying over sodium sulfate, the organic phase is concentrated. 66.45 g of 4-phenoxybutylmalonic acid ethyl ester of m.p. 69° to 72° C. are obtained.

Workup

  1. concentrationsubstantially concentrated in vacuo
  2. extractionthe aqueous mixture is extracted with 200 ml of diethyl ether
  3. temperaturewhile cooling with ice
  4. extractionextracted 3 times with 200 ml of diethyl ether each time
  5. dry with materialAfter drying over sodium sulfate
  6. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-478efae51057449cb27a2f190dec0086
Source dataset
uspto-grants-1982_06
Patent number
US04337267

Reaction notes

Loading…