Sodium Methoxide → Methyl 4-(hydroxymethyl)-3-methylbenzoate

HRID 501804Notes

Reaction equation

HRID 501804 reaction equation
C([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:16])(=O)C.C[O-].[Na+]>CO>[OH:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68460449Methyl 4-[(acetyloxy)methyl]-3-methylbenzoate

Product 1

HCID 19744381Methyl 4-(hydroxymethyl)-3-methylbenzoateYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

1.00 g of methyl 4-[(acetyloxy)methyl]-3-methylbenzoate was dissolved in 10 mL of methanol, to which a solution of 0.365 g of sodium methoxide in 7 mL of methanol was added dropwise at 5 to 7° C., and this solution was stirred for 30 minutes at 50° C. The reaction mixture was concentrated under reduced pressure, followed by successive addition of ethyl acetate and water, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 0.79 g of methyl 4-(hydroxymethyl)-3-methylbenzoate as yellow oil.

Workup

  1. additionwas added dropwise at 5 to 7° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionfollowed by successive addition of ethyl acetate and water
  4. customthe organic phase was separated
  5. washAfter the resultant organic phase was washed with water
  6. dry with materiala saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-bee935b7be6f4251bce4957c244d88e5
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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