Benzoic acid, 3-formyl-4-hydroxy-, methyl ester → Methyl 4-hydroxy-3-(hydroxymethyl)benzoate

HRID 636766Notes

Reaction equation

HRID 636766 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 12489759Methyl 4-hydroxy-3-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in (a) (1.80 g, 10 mmol) was mixed with 50 ml of methanol, and sodium borohydride (189 mg, 5 mmol) was added portionwise while maintaining the temperature below 20° C. After stirring for 5 minutes at room temperature, the methanol was evaporated off and the medium was then poured onto a 6N HCl/ice mixture, extracted with ethyl ether, washed with water to neutral pH, dried over magnesium sulfate and filtered, and the solvents were evaporated off. The properties of the final product were as follows:

Workup

  1. additionwas added portionwise
  2. temperaturewhile maintaining the temperature below 20° C
  3. customthe methanol was evaporated off
  4. additionthe medium was then poured onto a 6N HCl/ice mixture
  5. extractionextracted with ethyl ether
  6. washwashed with water to neutral pH
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvents were evaporated off

Sources & evidence

ORD record
ord-89fac22fc3704922a60112fb19a58941
Source dataset
uspto-grants-2001_02
Patent number
US06194450B1

Reaction notes

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