4-Hydroxybenzyl Alcohol → 4-Acetoxybenzyl alcohol

HRID 1609706Notes

Reaction equation

HRID 1609706 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11].C(OCC)C>[OH-].[K+]>[C:10]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 3283Diethyl EtherHCID 7918Acetic Anhydride

Product 1

HCID 959064-Acetoxybenzyl alcoholYield 45%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

8.4 g 4-hydroxybenzyl-alcohol, are dissolved in 11 ml 5.45M KOH, while cooling the reaction mixture with ice. 6.48 ml acetic anhydride are then added in 15 minutes to the solution obtained. An equal volume of ethyl ether is added, and once the organic phase is separated, it is washed with a NaHCO3 oversaturated solution and dried on anhydrous sodium sulphate and finally evaporated. The obtained product is then distilled (b.p. 140°-150° C.) under vacuum (3 mm Hg), then purified by silica gel chromatographic column (eluant cyclohexane/ethyl acetate 8: 2). A substantially pure product is obtained to be used for the successive reaction (yield 45%)

Workup

  1. temperaturewhile cooling the reaction mixture with ice
  2. customobtained
  3. customonce the organic phase is separated
  4. washit is washed with a NaHCO3 oversaturated solution
  5. dry with materialdried on anhydrous sodium sulphate
  6. customfinally evaporated
  7. distillationThe obtained product is then distilled (b.p. 140°-150° C.) under vacuum (3 mm Hg)
  8. custompurified by silica gel chromatographic column (eluant cyclohexane/ethyl acetate 8: 2)
  9. customA substantially pure product is obtained
  10. customto be used for the successive reaction (yield 45%)

Sources & evidence

ORD record
ord-194e2a0b3b8847edb7e9b74f18332038
Source dataset
uspto-grants-1995_03
Patent number
US05401853

Reaction notes

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