Butanedione → 3,5-Dimethyl-1-adamantanol

HRID 2302098

Reaction equation

HRID 2302098 reaction equation
C(C(C)=O)(C)=[O:2].[C:7]([C:10]12[CH2:20][C:14]3([CH3:21])[CH2:15][C:16]([CH3:19])([CH2:18][C:12]([C:22](=O)C)([CH2:13]3)[CH2:11]1)[CH2:17]2)(=[O:9])[CH3:8]>>[C:7]([C:10]12[CH2:20][C:14]3([CH3:21])[CH2:15][CH:16]([CH2:18][C:12]([CH3:22])([CH2:13]3)[CH2:11]1)[CH2:17]2)(=[O:9])[CH3:8].[C:7]([C:10]12[CH2:20][C:14]3([CH3:21])[CH2:13][C:12]([OH:2])([CH2:18][C:16]([CH3:19])([CH2:15]3)[CH2:17]1)[CH2:11]2)(=[O:9])[CH3:8].[CH3:21][C:14]12[CH2:15][C:16]3([OH:2])[CH2:17][CH:10]([CH2:11][C:12]([CH3:22])([CH2:18]3)[CH2:13]1)[CH2:20]2.[CH3:21][C:14]12[CH2:20][CH:10]3[CH2:17][CH:16]([CH2:18][C:12]([CH3:11])([C:7]3=[O:9])[CH2:13]1)[CH2:15]2

Participants

6

Reactant 2

HCID 650ButanedioneHCID 121131411,3-Diacetyl-5,7-dimethyladamantane

Product 4

HCID 2657933,5-Dimethyl-1-adamantanolYield 24%HCID 121131241-Acetyl-3,5-dimethyl AdamantaneYield 18%HCID 126443321,3-Dimethyl-4-adamantanoneYield 5%HCID 134640741-Acetyl-3,5-dimethyl-7-adamantanolYield 2%

Procedure

Except that the amount of biacetyl was changed to 18 mmol, the procedure of Example 8 was repeated to give 1-acetyl-3,5-dimethyladamantane (yield 18%, selectivity 29%), 1,3-diacetyl-5,7-dimethyladamantane (trace), 1-acetyl-3,5-dimethyl-7-adamantanol (yield 2%, selectivity 3%), 1,3-dimethyl-5-adamantanol (yield 24%, selectivity 38%), and 1,3-dimethyl-4-adamantanone (yield 5%, selectivity 38%), at a conversion rate from 1,3-dimethyladamantane of 63%.

Sources & evidence

ORD record
ord-ce7b2e3bac94428f99e301a037f86977
Source dataset
uspto-grants-2002_08
Patent number
US06429314B1

Linked notes

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