Hydrochloric Acid → 2,4-Pentanedione, 3-(p-hydroxybenzyl)-

HRID 1576946Notes

Reaction equation

HRID 1576946 reaction equation
CNC.[CH3:4][C:5](=[O:10])[CH2:6][C:7](=[O:9])[CH3:8].Cl.Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1>O>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH:6]([C:5](=[O:10])[CH3:4])[C:7](=[O:9])[CH3:8])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 31261AcetylacetoneHCID 356844-(Chloromethyl)phenol2×

Product 1

HCID 2038862,4-Pentanedione, 3-(p-hydroxybenzyl)-Yield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of p-chloromethyl phenol in acetonitrile (Example 12) was reacted with equimolar dimethyl amine and equimolar 2,4-pentanedione by stirring together for one hour. The reactive mixture was diluted with water, acidified with hydrochloric acid, extracted with ether, and then the ether extract was dried with sodium sulfate. The residual oil was triturated with benzene to yield 78% of 3(4' hydroxybenzyl)-2,4-pentanedione, M.P. 93°-94.5°C. Infrared and nuclear magnetic resonance spectra confirmed the identity of the product.

Workup

  1. extractionextracted with ether
  2. extractionthe ether extract
  3. dry with materialwas dried with sodium sulfate
  4. customThe residual oil was triturated with benzene

Sources & evidence

ORD record
ord-4793b7491f9244c88d5ba45693ad5c40
Source dataset
uspto-grants-1976_09
Patent number
US03983178

Reaction notes

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