Hydrochloric Acid → 3-(Benzyloxy)benzene-1,2-diol

HRID 267785Notes

Reaction equation

HRID 267785 reaction equation
COC1(C)[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]=2[O:4]1.Cl>CO>[CH2:13]([O:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:6]([OH:7])[C:5]=1[OH:4])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21553974HCID 21553974, compound

Product 1

HCID 119774353-(Benzyloxy)benzene-1,2-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-methoxy-2-methyl-4-benzyloxy-1,3-benzodioxole (13.6 g., 0.05 mole), methanol (210 ml.) and 5N hydrochloric acid (210 ml.) is stirred under reflux in an atmosphere of nitrogen for 10 hours. Most of the methanol is distilled off under vacuum and the product then extracted with ether. The ethereal solution is washed with water, dried over magnesium sulfate followed by calcium sulfate and evaporated to dryness to yield the crude 3-benzyloxy-catechol which can be recrystallized from di-isopropyl ether.

Workup

  1. temperatureunder reflux in an atmosphere of nitrogen for 10 hours
  2. distillationMost of the methanol is distilled off under vacuum
  3. extractionthe product then extracted with ether
  4. washThe ethereal solution is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-cf8fe09b4d854d44912f7654216a4cc3
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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