Hydrochloric Acid → 5-(Benzyloxy)-2-methoxybenzoic Acid

HRID 1288267Notes

Reaction equation

HRID 1288267 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:23]=[C:19]([C:20]([OH:22])=[O:21])[C:18]([OH:24])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S(OC)(OC)(=O)=O.[OH-].[Na+].Cl>O.C(O)C>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:1])=[C:19]([CH:23]=1)[C:20]([OH:22])=[O:21])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 118173925-(Benzyloxy)-2-hydroxybenzoic acid

Product 1

HCID 132820475-(Benzyloxy)-2-methoxybenzoic AcidYield 58.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Anhydrous potassium carbonate (60 g.) was added slowly with stirring to a refluxing mixture of 5-benzyloxysalicylic acid (13 g.; prepared as described by H. Bogeny and R. Krattner, Arch.Pharm; 1960, 293, 393) and anhydrous ethanol (250 ml.). Dimethyl sulphate (36 ml.) was then added, and the mixture stirred under reflux for 24 hours. The solid was filtered off, and the filtrate evaporated in vacuo to give more solid. The combined solids were suspended in water (250 ml.), and sodium hydroxide (20 g.) was added. The mixture was stirred under reflux for 2 hours, and then concentrated hydrochloric acid was added through the condenser, at such a rate that the contents of the flask continued to reflux gently, until pH 1 was attained. After being cooled, the solid which separated was filtered off, and recrystallised from 50% aqueous ethanol, and then from ethanol, to give 5-benzyloxy-2-methoxybenzoic acid (8 g.), m.p. 114°-116° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. filtrationThe solid was filtered off
  3. customthe filtrate evaporated in vacuo
  4. customto give more solid
  5. stirringThe mixture was stirred
  6. temperatureunder reflux for 2 hours
  7. temperatureto reflux gently, until pH 1
  8. temperatureAfter being cooled
  9. customthe solid which separated
  10. filtrationwas filtered off
  11. customrecrystallised from 50% aqueous ethanol

Sources & evidence

ORD record
ord-81d389fa6c4b459284d868c52b4a4f58
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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