Acetic Acid → 1,3-Dimethoxycarbonyl-5-adamantanol

HRID 1937245Notes

Reaction equation

HRID 1937245 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([O:17][CH3:18])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].C(O)(=[O:21])C>>[CH3:18][O:17][C:15]([C:7]12[CH2:8][C:9]3([OH:21])[CH2:10][CH:11]([CH2:12][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH2:14]3)[CH2:6]1)[CH2:13]2)=[O:16]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 365223Dimethyl 1,3-adamantanedicarboxylate

Product 1

HCID 120704691,3-Dimethoxycarbonyl-5-adamantanolYield 42%

Procedure

To 25 mL of acetic acid were added the 10 mmole of the 1,3-dimethoxycarbonyladamantane, 1 mmole of NHPI and 0.05 mmole of V(AA)3, and the resultant mixture was stirred for 8 hours at 85° C., under an oxygen atmosphere. As a result, 1,3-dimethoxycarbonyl-5-adamantanol (yield 42%) and 1,3-methoxycarbonyl-5,7-adamantanediol (yield 36%) were formed. The conversion of 1,3-dimethoxycarbonyladamantane was 92%.

Sources & evidence

ORD record
ord-df15937747a647da9375d77e2c1a06fc
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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