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

HRID 1834226Notes

Reaction equation

HRID 1834226 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 1 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-100b6ac469264b5d8143ac33a41b09f6
Source dataset
uspto-grants-1978_01
Patent number
US04069340

Reaction notes

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