Sodium Hydroxide → 4-(Benzyloxy)benzoic acid

HRID 976653Notes

Reaction equation

HRID 976653 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 299810Methyl 4-(benzyloxy)benzoate

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-benzyloxybenzoate (4.2 g, 17.3 mmole) and sodium hydroxide (15 mL of 2N) in methanol (200 mL) was heated at reflux for 24 hours. The methanol was removed under vacuum and water (200 mL) was added to the resulting residue. The mixture was acidified to pH 3 by the dropwise addition of concentrated hydrochloric acid. The resulting precipitate was isolated by filtration, washed with cold water and dried to provide 3.1 g of 4-benzyloxybenzoic acid as a white powder, m.p. 186°-187° C.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe methanol was removed under vacuum and water (200 mL)
  3. additionwas added to the resulting residue
  4. additionThe mixture was acidified to pH 3 by the dropwise addition of concentrated hydrochloric acid
  5. customThe resulting precipitate was isolated by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-ecf6d3426ab84496b6d0492c487a54c9
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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