Hydrogen Bromide → 4-Hydroxybenzoic Acid

HRID 1680978Notes

Reaction equation

HRID 1680978 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 74784-Methoxybenzoic Acid

Product 1

HCID 1354-Hydroxybenzoic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Next, the 4-methoxybenzoic acid (IV) was digested with HBr (20 ml) and glacial acetic acid (40 ml) overnight. Most of the acetic acid was distilled off and the remaining mixture was diluted with water. The precipitated benzoic acid was extracted in ether; the ether layer was dried with anhydrous MgSO4, filtered and rotary evaporated to produce 11.0 g of the 4-hydroxybenzoic acid (V).

Workup

  1. distillationMost of the acetic acid was distilled off
  2. additionthe remaining mixture was diluted with water
  3. extractionThe precipitated benzoic acid was extracted in ether
  4. dry with materialthe ether layer was dried with anhydrous MgSO4
  5. filtrationfiltered
  6. customrotary evaporated

Sources & evidence

ORD record
ord-c8f5804483b2464c9616b9b0a87c9314
Source dataset
uspto-grants-1992_12
Patent number
US05167855

Reaction notes

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