Acetic Acid → 3-(4-Hydroxyphenoxy)benzoic acid

HRID 1681550Notes

Reaction equation

HRID 1681550 reaction equation
C[O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.Br.C(O)(=O)C>O>[OH:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 6185083-(4-Methoxyphenoxy)benzoic acid

Product 1

HCID 1618523-(4-Hydroxyphenoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 73 g of 3-(4-methoxyphenoxy)benzoic acid, 300 ml of 48% hydrobromic acid, and 600 ml of acetic acid was heated at reflux for 48 hours. The reaction mixture was allowed to cool to ambient temperature, poured into cold water, and extracted with ethyl acetate. The organic extracts were dried and concentrated in vacuo. The residue was crystallized from ethyl/hexane providing 39.41 g of the desired subtitle intermediate, m.p. 172°-174° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from ethyl/hexane providing 39.41 g of the desired subtitle intermediate, m.p. 172°-174° C.

Sources & evidence

ORD record
ord-485bff835e834f9ab8bca3cedf10b143
Source dataset
uspto-grants-1992_12
Patent number
US05171882

Reaction notes

Loading…