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

HRID 1901140Notes

Reaction equation

HRID 1901140 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[OH-].[Na+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH2:15]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8468Vanillic AcidHCID 14798Sodium Hydroxide2×

Product 1

HCID 2263354-(Benzyloxy)-3-methoxybenzoic acidYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-hydroxy-3-methoxybenzoic acid (25 g, 0.15 mole) in ethanol (150 ml), 2N NaOH aq. (74.3 g, 0.15 mole) and benzyl chloride (56.5 g, 0.45 mole) were added, continued to stir for 1 hour under reflux. Then, 5N NaOH aq. (150 ml) was added dropwise with stirring under reflux, and continued to stir for 1 hour under reflux. After reaction, the solvent was removed, and H2O was added to the residue and acidified with conc. hydrochloric acid to make pH 1. The precipitate was filtered, washed with H2O and dried to give 22.1 g of 4-benzyloxy-3-methoxybenzoic acid as pale yellow crystals having a m.p. of 171°-172.5° C.

Workup

  1. additionwere added
  2. temperatureunder reflux
  3. stirringwith stirring
  4. temperatureunder reflux
  5. stirringto stir for 1 hour
  6. temperatureunder reflux
  7. customAfter reaction
  8. customthe solvent was removed
  9. additionH2O was added to the residue
  10. filtrationThe precipitate was filtered
  11. washwashed with H2O
  12. customdried

Sources & evidence

ORD record
ord-08aecae92d6743ad8bcfe872e50a9f9f
Source dataset
uspto-grants-1996_11
Patent number
US05576359

Reaction notes

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