Hydrochloric Acid → Adamantane-1,4-diol

HRID 1752308

Reaction equation

HRID 1752308 reaction equation
[BH4-].[Na+].[OH:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([C:7]3=[O:14])[CH2:5]1)[CH2:11]2.Cl>CO>[C:4]12([OH:3])[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH:7]3[OH:14])[CH2:5]1)[CH2:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 64184IdramantoneHCID 4311764Sodium borohydride

Product 1

HCID 4252005Adamantane-1,4-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (3.00 g) is added in three equal portions to a solution of 5-hydroxy-adamantan-2-one (5.00 g) in methanol (100 mL) chilled in an ice bath. The mixture is stirred in the cooling bath for 1 h and at room temperature overnight. 1 M hydrochloric acid is added and the resulting mixture is stirred for 0.5 h. The mixture is concentrated, water is then added to the residue, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (MgSO4), and concentrated to give the title compound as a mixture of diastereomers (ca. 1:1). Yield: 3.20 g (63% of theory); Mass spectrum (ESI+): m/z=186 [M+NH4]+.

Workup

  1. temperaturechilled in an ice bath
  2. stirringthe resulting mixture is stirred for 0.5 h
  3. concentrationThe mixture is concentrated
  4. additionwater is then added to the residue
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. extractionThe combined extract
  7. washis washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1213e1f4b2cc4e078632bce8edeca8f8
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Linked notes

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