N-Hydroxyphthalimide → 5-Hydroxy-1,3-adamantanedicarboxylic acid

HRID 1699155Notes

Reaction equation

HRID 1699155 reaction equation
[C:1]12([C:14]([OH:16])=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11]([OH:13])=[O:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:17]N1C(=O)C2=CC=CC=C2C1=O>[Co+2].C(O)(=O)C>[OH:17][C:5]12[CH2:4][C:3]3([C:11]([OH:13])=[O:12])[CH2:9][CH:7]([CH2:8][C:1]([C:14]([OH:16])=[O:15])([CH2:2]3)[CH2:10]1)[CH2:6]2

Participants

5

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 643391,3-Adamantanedicarboxylic acid2×

Product 1

HCID 120106445-Hydroxy-1,3-adamantanedicarboxylic acidYield 52.5%

Reagents, catalysts & solvents 2

HCID 104729Cobalt(2+)CatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.92 mol of 1,3-adamantanedicarboxylic acid, 192 mmol of N-hydroxyphthalimide, 1.83 mmol of cobalt (II) acetylacetonato and 1290 ml of acetic acid was stirred at 80° C. under an oxygen atmosphere (1 atm) for 24 hours. The reaction mixture was concentrated and then separated by the addition of ethyl acetate and water. Sodium chloride was added to the aqueous layer and the layer was extracted with ethyl acetate; the organic layer was dried on anhydrous magnesium sulfate and was concentrated. The caked crude purified product was washed with ethyl acetate to give 5-hydroxy-1,3-adamantanedicarboxylic acid (yield: 52.5%) at a conversion rate from 1,3-adamantanedicarboxylic acid of 75%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customseparated by the addition of ethyl acetate and water
  3. additionSodium chloride was added to the aqueous layer
  4. extractionthe layer was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried on anhydrous magnesium sulfate
  6. concentrationwas concentrated
  7. custompurified product
  8. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-44422155e8454488b2d60145addef73d
Source dataset
uspto-grants-2002_02
Patent number
US06344590B1

Reaction notes

Loading…