Acetic Acid → HCID 85744319, compound

HRID 618990Notes

Reaction equation

HRID 618990 reaction equation
[CH:1]12[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1.[OH:12]N1[C:17](=O)[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].[C:24]([OH:27])(=O)[CH3:25]>>[OH:12][C:1]12[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1.[OH:23][C:14]12[CH2:15][CH:16]([CH2:17][CH2:1]1)[CH:19]1[CH2:25][C:24]2([OH:27])[CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10665N-HydroxyphthalimideHCID 13070377HCID 13070377, compound2×

Product 2

HCID 13070378HCID 13070378, compoundYield 24%HCID 85744319HCID 85744319, compoundYield 75%

Procedure

To 10 milliliters of acetic acid were added 1.5 grams (10 millimoles) of tricyclo[4.3.1.12,5 ]undecane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred under an oxygen atmosphere at 75° C. for 15 hours. As a result, tricyclo[4.3.1.12,5 ]undecane was transformed, with a transformation rate of 99%, into 1-hydroxytricyclo[4.3.1.12.5 ]undecane (selectivity for tricyclo[4.3.1.12,5 ]undecane 24%, yield 24%) and dihydroxy-tricyclo[4.3.1.12,5 ]undecane (selectivity for tricyclo[4.3.1.12,5 ]undecane 75%, yield 75%). A selectivity for the alcohols was 99 percent.

Sources & evidence

ORD record
ord-7122716644914edda93875fadc37cdcb
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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