Methanol → 3-(Hydroxymethyl)-2-methylphenol

HRID 1250095Notes

Reaction equation

HRID 1250095 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].B.CO>O1CCCC1>[OH:6][CH2:5][C:4]1[C:3]([CH3:11])=[C:2]([OH:1])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 130594263-(Hydroxymethyl)-2-methylphenolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-hydroxy-2-methylbenzoic acid (44.4 g, 285 mmol) (prepared as described in Preparation 1A) dissolved in dry tetrahydrofuran (200 mL) was added to 1 M borane in tetrahydrofuran (800 mL) while stirring at a temperature of 0° C. The resulting semisolid mixture was heated in a mantle to just short of reflux and heating was maintained for about 15 hours. Methanol (200 mL) was added to the reaction mixture. The resultant clear solution was evaporated in vacuo and then evaporated with further portions of methanol to give 3-hydroxymethyl-2-methylphenol (30.3 g, 99%).

Workup

  1. temperatureThe resulting semisolid mixture was heated in a mantle to just short
  2. temperatureof reflux
  3. temperatureheating
  4. temperaturewas maintained for about 15 hours
  5. customThe resultant clear solution was evaporated in vacuo
  6. customevaporated with further portions of methanol

Sources & evidence

ORD record
ord-f096362f70da41e1bdeaedca964bc632
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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