Ethanol → 4-(Tetrahydropyran-2-yloxy)phenylethanol

HRID 344794Notes

Reaction equation

HRID 344794 reaction equation
C([O:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([O:18][CH2:19][CH3:20])[CH3:17])=[CH:11][CH:10]=1)[CH3:8])(=O)CCC.[BH4-].[Na+].[CH2:23](O)C>>[O:18]1[CH2:19][CH2:20][CH2:23][CH2:17][CH:16]1[O:15][C:12]1[CH:11]=[CH:10][C:9]([CH:7]([OH:6])[CH3:8])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 544848551-(4-(1-Ethoxyethoxy)phenyl)ethyl butyrate

Product 1

HCID 539473164-(Tetrahydropyran-2-yloxy)phenylethanolYield 88%

Procedure

In 200 ml of ethanol was dissolved 22.0 g (0.1 mole) of 4-(tetrahydro-2-pyranyloxy)acetophenone obtained in Example 4 (i), to which 2.3 g (58 millimoles) of NaBH4 was added, and the mixture was subjected to reaction for 3 hours at 25° C. After ethanol was distilled under reduced pressure, 200 ml of ethanol was added thereto, and it was washed with diluted hydrochloric acid, then water and finally an aqueous solution of sodium hydrogencarbonate. The resulting ether layer was dried with anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure to give 19.5 g of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethanol (yield: 88%).

Workup

  1. customthe mixture was subjected to reaction for 3 hours at 25° C
  2. distillationAfter ethanol was distilled under reduced pressure, 200 ml of ethanol
  3. additionwas added
  4. washit was washed with diluted hydrochloric acid
  5. dry with materialThe resulting ether layer was dried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-8c5072aa74a24ffc966ca4524e053799
Source dataset
uspto-grants-1991_10
Patent number
US05053507

Reaction notes

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