Methyl 4-methoxy-2-methylbenzoate → 4-Methoxy-2-methylbenzyl alcohol

HRID 1522865Notes

Reaction equation

HRID 1522865 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[C:5]([CH3:13])[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[C:5]([CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 13257269Methyl 4-methoxy-2-methylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 27595864-Methoxy-2-methylbenzyl alcoholYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-methoxy-2-methylbenzoate (11.4 g, 63.3 mmol) in THF (65 mL) at 0° C., LiAlH4 (1M in ether, 76.0 mL, 75.9 mmol) was added via addition funnel over 50 min. The ice water bath was removed, and the reaction was allowed to stir at room temperature for 30 min. Upon completion, the reaction was cooled to 0° C. and sodium sulfate decahydrate was added portionwise until the bubbling ceased. The reaction was then diluted with ether and filtered. The filtrate was concentrated under reduced pressure to give (4-methoxy-2-methylphenyl)methanol (8.2 g) as a clear oil. 1H NMR (300 MHz, CDCl3): δ 7.23 (d, 1H), 6.72 (m, 2H), 4.63 (d, 2H), 3.79 (s, 3H), 2.36 (s, 3H), 1.42 (t, 1H).

Workup

  1. customThe ice water bath was removed
  2. temperatureUpon completion, the reaction was cooled to 0° C.
  3. additionsodium sulfate decahydrate was added portionwise until the bubbling
  4. additionThe reaction was then diluted with ether
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3051272714544d138f32571854d897e0
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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