Hydrochloric Acid → 1-(1-Adamantyl)ethanol

HRID 2302107Notes

Reaction equation

HRID 2302107 reaction equation
[BH4-].[Na+].[C:3]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2)(=[O:5])[CH3:4].[OH-].[Na+].Cl>O.CO>[OH:5][CH:3]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2)[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 123126Methyl tricyclo(3.3.1.13,7)dec-1-yl ketoneHCID 4311764Sodium borohydride

Product 1

HCID 27697131-(1-Adamantyl)ethanolYield 98.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Powdery sodium borohydride (4.8 g) was added slowly over 30 minutes to a mixture of 45.0 g of 1-acetyladamantane, 100 ml of methanol, and 20 ml of 0.1 N sodium hydroxide on a water bath. The resultant mixture was further stirred for 30 minutes, was neutralized with a 1 N hydrochloric acid aqueous solution, and 200 ml of water was added to the mixture. The obtained crystals were filtrated, was washed with water and was dried in vacuo to give 45.0 g of 1-(1-hydroxyethyl)adamantane. To this were added 400 ml of toluene, 4.9 g of 98% sulfuric acid, and 0.1 g of hydroquinone, and the resultant mixture was stirred for 3 hours with azeotropic distillation and dehydration. The reaction mixture was cooled, washed with saturated aqueous sodium bicarbonate and saturated sodium chloride aqueous solution, and was concentrated. The obtained concentrate was distilled to give 29.0 g (yield 72.5%) of 1-vinyladamantane (65° C./4 mm Hg).

Workup

  1. additionwas added to the mixture
  2. filtrationThe obtained crystals were filtrated
  3. washwas washed with water
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-902bef281da643aa9e908090841ef07c
Source dataset
uspto-grants-2002_08
Patent number
US06429314B1

Reaction notes

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