Hydrochloric Acid → 1-(1-Naphthyl)ethanol

HRID 1382237

Reaction equation

HRID 1382237 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].Cl>C(O)C.O>[OH:5][CH:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 136631-AcetylnaphthaleneHCID 4311764Sodium borohydride

Product 1

HCID 980301-(1-Naphthyl)ethanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (2.1 g) was added to a solution of 1-acetylnaphthalene (18.86 g) in ethanol (200 ml) at room temperature and the mixture was stirred at the same temperature for 2 hours. The mixture was diluted with water (50 ml), acidified to pH 3 with 1N hydrochloric acid and concentrated to about 70 ml. The concentrate was extracted with ethyl acetate (100 ml×2). The extract was dried over magnesium sulfate and evaporated to give 1-(1-hydroxyethyl)naphthalene as an oil which was used in a next reaction without further purification. Hydrogen bromide was bubbled into a solution of 1-(1-hydroxyethyl)naphthalene (18.96 g) in ether (180 ml) for 2 hours under ice-bath cooling. The reaction mixture was washed with water (50 ml×2), 2.5% sodium bicarbonate (50 ml×2) and water (50 ml×2), dried over magnesium sulfate and evaporated to give 1-(1-bromoethyl)naphthalene (22.63 g).

Workup

  1. concentrationconcentrated to about 70 ml
  2. extractionThe concentrate was extracted with ethyl acetate (100 ml×2)
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-ec0c0cc168be4c99951bf644adf7ac3f
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Linked notes

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