Diethyl Ether → Benzeneethanol, 4-(acetyloxy)-

HRID 1595511

Reaction equation

HRID 1595511 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C(OCC)C>O.O1CCCC1>[CH3:14][C:13]([O:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1)=[O:15]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 10393TyrosolHCID 14797Potassium Hydroxide

Product 1

HCID 586676Benzeneethanol, 4-(acetyloxy)-Yield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5.6 g (0.1 mole) potassium hydroxide in 10 ml water was added to a cooled solution of 13.8 g (0.1 mole) p-hydroxyphenethyl alcohol in 50 ml tetrahydrofuran. 10.2 g (0.1 mole) acetic anhydride was slowly added under stirring. After 2 hours diethyl ether and water were added. The phases were separated and the organic phase was dried, filtered and evaporated in vacuo. The product contained 15% starting material and was therefore redissolved in diethyl ether and washed twice with dilute sodium carbonate. Drying, filtration and evaporation of solvents in vacuo gave 12 g (yield 67%) of 2-(4-methylcarbonyloxyphenyl)-1-ethanol which was used without further purification.

Workup

  1. customThe phases were separated
  2. customthe organic phase was dried
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionwas therefore redissolved in diethyl ether
  6. washwashed twice with dilute sodium carbonate
  7. customDrying
  8. filtrationfiltration and evaporation of solvents in vacuo

Sources & evidence

ORD record
ord-ecd20afd2ef34717a3827cdc48a36da5
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Linked notes

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