Hydrochloric Acid → Methyl 2-hydroxy-5-(hydroxymethyl)benzoate

HRID 1451077Notes

Reaction equation

HRID 1451077 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[OH:6].[BH4-].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:5]=1[OH:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 14363598Methyl 5-Formylsalicylate

Product 1

HCID 19977478Methyl 2-hydroxy-5-(hydroxymethyl)benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl-5-formylsalicylate (Kadaba, J. Pharm. Sci. 1974, 63, 1333-1335) (1.80 g, 0.01 mol) in methanol (20 mi) at 0° C. was added sodium borohydride (0.38 g, 0.01 mol) in 4 portions during 0.5 h. The solution was further stirred at 0° C. for 2 h and then at room temperature for 0.3 h. It was neutralized with hydrochloric acid and concentrated under vacuum. The residue was passed through a column of silica gel using 1:1 ethyl acetate:hexane as the eluent to give 1.0 g (55%) of methyl-2-hydroxy-5-hydroxymethylbenzoate as a pale yellow powder, mp 66°-67° C.

Workup

  1. waitat room temperature for 0.3 h
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-52b28c868c9e48bb8a48ab72f24bf54d
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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