4-Hydroxybenzyl Alcohol → 4-Acetoxybenzyl alcohol

HRID 2361623Notes

Reaction equation

HRID 2361623 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>C(OCC)(=O)C>[C:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 6367Acetyl chlorideHCID 8471Triethylamine

Product 1

HCID 959064-Acetoxybenzyl alcoholYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a cooled suspension of 4-hydroxybenzyl alcohol (1.95 g, 14 mmol) in ethyl acetate (25 mL) in an ice-bath, triethylamine (2.1 mL, 14.9 mmol) was added in one lot under stirring. A solution of acetyl chloride (1.1 mL, 15.5 mmol) in ethyl acetate (12 mL) was added dropwise from an addition funnel. The reaction mixture was stirred overnight. The solid was filtered, washed with ethyl acetate and the residue, after concentration, was purified by column chromatography using hexanes initially and later gradually to 40% ethyl acetate. Yield 40%. 1H-NMR (CDCl3), δ 2.02 (br. s, 1H), 2.29 (s, 3H), 4.65 (s, 2H), 7.07 (d, 2H), 7.36 (d, 2H).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationThe solid was filtered
  3. washwashed with ethyl acetate
  4. concentrationthe residue, after concentration
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6cd30e62858e47ab9d59fae73f812889
Source dataset
uspto-grants-2014_04
Patent number
US08691787B2

Reaction notes

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