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

HRID 2368912Notes

Reaction equation

HRID 2368912 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-6fab1e72f7b24b2094cc286839f34479
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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