Water → (2-Ethyl-4-methylphenyl)methanol

HRID 878674Notes

Reaction equation

HRID 878674 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[CH2:5][OH:6])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68288774Methyl 2-ethyl-4-methylbenzoate

Product 1

HCID 68301223(2-Ethyl-4-methylphenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound methyl 2-ethyl-4-methylbenzoate (646 mg, 3.65 mmol) in THF (6 mL) cooled to −50° C., was added LiAlH4 (277 mg, 7.30 mmol) in portions. The mixture was stirred at this temperature for 1 h. Added water (0.3 mL) slowly, followed by NaOH (aq, 10%, 0.3 mL) and water (0.9 mL), the resulting mixture was filtered and washed with THF, concentrated the filtrate to give 518 mg of the title compound (95%). 1H NMR (400 MHz, CDCl3): δ 1.23 (3H, t, J=7.2 Hz), 1.54 (1H, s), 2.33 (3H, s), 2.68 (2H, q, J=7.6 Hz), 4.67 (2H, s), 7.01 (1H, d, J=8.0 Hz), 7.03 (1H, s), 7.23 (1H, d, J=7.6 Hz).

Workup

  1. filtrationthe resulting mixture was filtered
  2. washwashed with THF
  3. concentrationconcentrated the filtrate

Sources & evidence

ORD record
ord-628d91b2665d46c0a25a7bee5a0bee47
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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