Water → (3-Chloro-4-ethylphenyl)methanol

HRID 514440Notes

Reaction equation

HRID 514440 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13])[C:5](OC)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 81445331HCID 81445331, compound

Product 1

HCID 86725560(3-Chloro-4-ethylphenyl)methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-chloro-4-ethylbenzoate (367 mg, 1.85 mmol) in THF (5 mL) that cooled to −50° C., LiAlH4 (141 mg, 2.70 mmol) was added in portions. After which, the mixture was stirred at this temperature for 1 h. Added water (0.2 mL) slowly, followed by NaOH (aq, 10%, 0.2 mL) and water (0.6 mL), the resulted mixture was filtered and washed with THF, concentrated the filtrate to give 308 mg of the title compound (98%). 1H NMR (400 MHz, CDCl3): δ 1.22 (3H, t, J=7.6 Hz), 2.74 (2H, q, J=7.6 Hz), 4.63 (2H, d, J=5.2 Hz), 7.17-7.23 (2H, m), 7.35 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-29db6d474efe441eb987a56a4e8a5e98
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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