Hydrochloric Acid → 3,5-Dihydroxyadamantane-1-carboxylic acid

HRID 1470045

Reaction equation

HRID 1470045 reaction equation
[OH-:1].[K+].[Mn]([O-])(=O)(=O)=O.[K+].Br[C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][C:12]([C:20]([OH:22])=[O:21])([CH2:13]3)[CH2:11]1)[CH2:17]2.Cl.S(=O)(O)[O-:25].[Na+]>O>[OH:1][C:14]12[CH2:15][CH:16]3[CH2:17][C:10]([OH:25])([CH2:11][C:12]([C:20]([OH:22])=[O:21])([CH2:18]3)[CH2:13]1)[CH2:19]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 308183-Bromoadamantane-1-carboxylic acidHCID 516875Potassium PermanganateHCID 23665763Sodium Bisulfite

Product 1

HCID 120106473,5-Dihydroxyadamantane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
98 °C

Procedure

To a mixture of potassium hydroxide (130 mg, 2.0 mmol) and potassium permanganate (350 mg, 2.2 mmol) in H2O (10 mL) at 50° C. was added 3-bromo-adamantane-1-carboxylic acid (512 mg, 2.0 mmol). The reaction mixture was heated at 98° C. for 18 hours. After cooling to ambient temperature, the mixture was acidified by the addition of 6 N aqueous HCl, then saturated aqueous sodium bisulfite was added. The mixture was extracted with 2-propanol/CH2Cl2 (1:3). The organic extract was concentrated to afford the title compound.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionThe mixture was extracted with 2-propanol/CH2Cl2 (1:3)
  3. extractionThe organic extract
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-5dd14d8110704f46a344318ca90c6f9d
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Linked notes

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