N-Hydroxyphthalimide → 3-Hydroxyadamantane-1-carboxylic acid

HRID 1699152Notes

Reaction equation

HRID 1699152 reaction equation
[C:1]12([C:11]([OH:13])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:14]N1C(=O)C2=CC=CC=C2C1=O>[Co+2].C(O)(=O)C>[OH:14][C:3]12[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][C:1]([C:11]([OH:13])=[O:12])([CH2:8]3)[CH2:2]1)[CH2:4]2

Participants

5

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 132351-Adamantanecarboxylic acid2×

Product 1

HCID 27365183-Hydroxyadamantane-1-carboxylic acidYield 38%

Reagents, catalysts & solvents 2

HCID 104729Cobalt(2+)CatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5.07 mol of 1-adamantanecarboxylic acid, 507 mmol of N-hydroxyphthalimide, 5.07 mmol of cobalt (II) acetylacetonato and 12500 ml of acetic acid was stirred at 75° C. under an oxygen atmosphere (1 atm) for 8 hours. The reaction mixture was concentrated, and was subjected to column chromatography on a silica gel (eluent: chloroform/methanol (8/1)), and the obtained purified product was further recrystallized with ethanol/n-hexane to give 3-hydroxy-1-adamantanecarboxylic acid (yield: 38%) at a conversion rate from 1-adamantanecarboxylic acid of 99%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained purified product
  3. customwas further recrystallized with ethanol/n-hexane

Sources & evidence

ORD record
ord-f02ce9154ee4486bb7c1fa88e552a296
Source dataset
uspto-grants-2002_02
Patent number
US06344590B1

Reaction notes

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