Hydroxyphenylacetic acid → HCID 12531839, compound

HRID 1863284Notes

Reaction equation

HRID 1863284 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.ClC1C=CC([CH2:19][S:20]([CH2:23][C:24]2[CH:29]=CC(Cl)=CC=2)(=[O:22])=[O:21])=CC=1.[C:31](=O)([O-])[O-].[K+].[K+].CN(C)[C:39](=[O:41])[CH3:40]>O>[CH3:19][S:20]([C:23]1[CH:24]=[CH:29][C:39]([O:41][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)=[CH:40][CH:31]=1)(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 346670Bis[4-chlorobenzyl]sulfone

Product 1

HCID 12531839HCID 12531839, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30.4 g of p-hydroxyphenylacetic acid, 38.12 g of p-chlorophenyl methylsulfone, 55.2 g of potassium carbonate and 250 ml of N,N-dimethylacetamide is heated under Argon overnight at 150°-155° C. with vigorous stirring. The mixture is cooled, diluted with 500 ml of H2O, and extracted with two 200 ml portions of benzene. Acidification of the aqueous layer affords an amber oil which solidifies to a white solid, mp 122.5°-125° C. Recrystallization from chloroform affords the product as white needles, mp 127.5°-129.5° C.

Workup

  1. temperatureis heated under Argon overnight at 150°-155° C. with vigorous stirring
  2. temperatureThe mixture is cooled
  3. extractionextracted with two 200 ml portions of benzene
  4. customAcidification of the aqueous layer affords an amber oil which
  5. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-7310876f17aa4b1e915af17950f3969f
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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