Acetic Acid → Bicyclo[2.2.1]heptane-1,2-diol

HRID 618989Notes

Reaction equation

HRID 618989 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[OH:8]N1[C:13](=[O:14])[C:12]2=CC=[CH:17][CH:18]=[C:11]2C1=O.O=O.[C:22]([OH:25])(=O)[CH3:23]>>[OH:8][C:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[OH:25][C:22]12[CH2:23][CH:11]([CH2:18][CH2:17]1)[CH2:12][CH:13]2[OH:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 9233Bicyclo(2.2.1)heptane2×HCID 10665N-Hydroxyphthalimide

Product 2

HCID 524266Bicyclo[2.2.1]heptan-1-olYield 44%HCID 19960695Bicyclo[2.2.1]heptane-1,2-diolYield 55%

Procedure

A mixture of 0.96 gram (10 millimoles) of norbornane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 10 milliliters of acetic acid was stirred in an oxygen atmosphere at a temperature of 75° C. for 15 hours to give 1-hydroxynorbornane (selectivity for norbornane 44%, yield 44%) and 1,2-dihydroxynorbornane (selectivity for norbornane 55%, yield 55%) with a transformation rate of norbornane of 99% and the selectivity for the alcohols of 99%.

Sources & evidence

ORD record
ord-ebbee50fe7934b388d26ba657215c847
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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