Protocatechuic Acid → 3,4-Bis(benzyloxy)benzoic acid

HRID 1440440Notes

Reaction equation

HRID 1440440 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(O)C.[OH-].[Na+]>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1)[C:5]([OH:7])=[O:6])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 72Protocatechuic AcidHCID 313Hydrochloric AcidHCID 7503Benzyl Chloride

Product 1

HCID 108541553,4-Bis(benzyloxy)benzoic acidYield 138.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a suspension of 3,4-dihydroxybenzoic acid (25.4 g, 0.17 mle) in ethanol (250 ml), 5N NaOH aq. (270 ml) and benzyl chloride (102 g, 0.81 mole) were added. The resulting mixture was reacted with stirring for 6 hours under reflux. The reaction mixture was cooled to room temperature, allowed to stand at same temperature overnight and acidified with conc. hydrochloric acid (40 ml). The precipitate was filtered, washed with hot ethanol and dried under reduced pressure to give 38.2 g of 3,4-dibenzyloxybenzoic acid as pale yellow crystals having a m.p. of 184°-186° C.

Workup

  1. additionwere added
  2. customThe resulting mixture was reacted
  3. temperatureunder reflux
  4. customto stand at same temperature overnight
  5. filtrationThe precipitate was filtered
  6. washwashed with hot ethanol
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-738ddf71ddc542a8908cfaec805fb44e
Source dataset
uspto-grants-1996_03
Patent number
US05498748

Reaction notes

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