3-Hydroxy-2-methylbenzoic Acid → 3-(Hydroxymethyl)-2-methylphenol

HRID 594981Notes

Reaction equation

HRID 594981 reaction equation
B.O1CCCC1.[CH3:7][C:8]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].C(=O)([O-])O.[Na+]>C1COCC1>[OH:11][CH2:10][C:9]1[C:8]([CH3:7])=[C:16]([OH:17])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 2520233-Hydroxy-2-methylbenzoic AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 130594263-(Hydroxymethyl)-2-methylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran (1M in THF, 4.6 mL, 1.4 eq) was added to a solution of 2-methyl-3-hydroxybenzoic acid (0.50 g, 3.3 mmol) in THF (30 mL). The reaction mixture was stirred overnight at rt before addition of saturated sodium hydrogencarbonate. The aqueous phase was extracted with DCM. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford 3-(hydroxymethyl)-2-methylphenol in a quantitative yield.

Workup

  1. extractionThe aqueous phase was extracted with DCM
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12fa9358b3b44cd19b4bd0bfd2db8199
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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