Ethanol → Methyl 4-(hydroxymethyl)-2-methylbenzoate

HRID 1501002Notes

Reaction equation

HRID 1501002 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1)=[O:2].[BH4-].[Na+].C(O)C>O>[OH:2][CH2:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 20134203Methyl 4-formyl-2-methylbenzoate

Product 1

HCID 23021531Methyl 4-(hydroxymethyl)-2-methylbenzoateYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-formyl-2-methylbenzoate (200 mg, 1.1 mmol), sodium borohydride (210 mg, 5.5 mmol) and ethanol (10 mL) was stirred at room temperature for 4 hours. To the resultant mixture, water (0.4 mL) was added. The organic phase was separated, concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give methyl 4-(hydroxymethyl)-2-methylbenzoate (126 mg, 64%). 1H NMR (300 MHz, d6-DMSO): δ 7.78 (d, J=7.8 Hz, 1H), 7.15 (dd, J=7.8 Hz, J=1.8 Hz, 1H), 7.06 (d, J=1.8 Hz, 1H), 5.39 (t, J=5.7 Hz, 1H), 4.79 (d, J=5.7 Hz, 2H), 3.88 (s, 3H), 2.35 (s, 3H).

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-11424d351cfe4533b94793e2caed9161
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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