3-Hydroxybenzyl alcohol → 4-Hydroxymethylsalicylate

HRID 1827958Notes

Reaction equation

HRID 1827958 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10](=O)([O-:12])[O-:11].[K+].[K+].Cl>O>[OH:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 313Hydrochloric AcidHCID 11430Potassium Carbonate

Product 1

HCID 6568834-Hydroxymethylsalicylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-hydroxybenzylalcohol (10 g, 80 mmol) and potassium carbonate (33.35 g, 240 mmol) were stirred under carbon dioxide in a sealed vessel at 1500-2000 psi and 150° C. for 18 hours. The cooled residue was dissolved in water, acidified to pH 1 using concentrated hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and evaporated under reduced pressure. The product was recrystallised from cyclohexane to afford the title compound, 740 mg.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe product was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-492ed237bd544060b08ec3a44e1f8e30
Source dataset
uspto-grants-2006_06
Patent number
US07056934B2

Reaction notes

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