Benzyl Chloride → 4-(Benzyloxy)-3-methoxybenzoic acid

HRID 411990

Reaction equation

HRID 411990 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[O:19][CH3:20]>C1COCC1.[OH-].[Na+]>[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 8468Vanillic Acid

Product 1

HCID 2263354-(Benzyloxy)-3-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of benzyl chloride (24.6 ml, 209 mmol, 1.1 eq.) in THF (100 ml) was added dropwise at 0° C. over 15 min, to a mechanically stirred solution of 4-hydroxy-3-methoxybenzoic acid (vanillic acid, 1) (30 g, 179 mmol) in THF (90 ml) and 2.0 M aq. NaOH (225 ml). The mixture was allowed to warm to room temperature and then heated under reflux for 48 hours. After cooling, the mixture was washed with hexane (2×100 ml) and the THF was removed in vacuo. The remaining aqueous phase was acidified to pH 1 with conc. HCl. The resulting precipitate was collected by filtration, washed with water and dried to afford 4-benzyloxy-3-methoxybenzoic acid (2) as a pale amorphous solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 hours
  3. temperatureAfter cooling
  4. washthe mixture was washed with hexane (2×100 ml)
  5. customthe THF was removed in vacuo
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7ed0159312694b40864f40004b98254f
Source dataset
uspto-grants-2003_05
Patent number
US06562806B1

Linked notes

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