4'-Phenoxyacetophenone → 4-Phenoxybenzoic acid

HRID 1632331Notes

Reaction equation

HRID 1632331 reaction equation
Cl[O-:2].[Na+].[O:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])C)=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CC(C)=O>[O:4]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:2])=[CH:15][CH:16]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 2367834'-PhenoxyacetophenoneHCID 23665760Sodium Hypochlorite

Product 1

HCID 751824-Phenoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In each case a 5.25% sodium hypochlorite solution (85.1 g.: 0.060 mole) was added slowly in portions to a solution of 3.18 g. (0.0150 mole) the p-phenoxyacetophenone sample while heating from 40° to 100° C. The resulting solution was concentrated at 100° C., producing a crystalline precipitate. Acetone was then added to consume excess sodium hypochlorite followed by boiling, acidification with some excess concentrated hydrochloric acid (10 ml of 12N), stirring, filtration, water wash and then drying at 70° C./under vacuum for about 1 hr. The p-phenoxybenzoic acid obtained from the p-phenoxyacetephenone produced in the presence of hydrogen fluoride was white with a melting point of 159°-162° C. In contrast, the p-phenoxybenzoic acid produced in the presence of aluminum trichloride had a yellow (or light beige) discoloration and a strongly depressed melting point of 137°-149° C., indicating presence of considerable impurities.

Workup

  1. concentrationThe resulting solution was concentrated at 100° C.
  2. customproducing a crystalline precipitate
  3. customto consume excess sodium hypochlorite
  4. filtrationfiltration, water
  5. washwash
  6. customdrying at 70° C./under vacuum for about 1 hr

Sources & evidence

ORD record
ord-be602aca0616451c826bf37f511eff9c
Source dataset
uspto-grants-1984_10
Patent number
US04474990

Reaction notes

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