Diethyl Ether → 4-Methyl-3-methylene-1-isopropenyl cyclohexane

HRID 231934

Reaction equation

HRID 231934 reaction equation
[CH3:1][C@H:2]1[C:7](=O)[CH2:6][C@H:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH2:3]1.[CH3:12]COCC>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:9]([CH3:11])=[CH2:10])[CH2:6][C:7]1=[CH2:12]

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 22227(+)-Dihydrocarvone

Product 1

HCID 147660024-Methyl-3-methylene-1-isopropenyl cyclohexaneYield 95%

Procedure

BDAM (2.60 grams) was combined with ether (2 milliliters) and TMAL (1.0 milliliter) as described in Example 4, after which 1.50 grams of (+) dihydrocarvone were added. As in Example 4, a noticeable exotherm was observed. After 3 hours of stirring at room temperature, the reaction mixture was hydrolyzed as in Example 1. After the usual work up and column separation, 1.40 grams of 4-methyl-3-methylene-1-isopropenyl cyclohexane were isolated (95% yield).

Workup

  1. customAfter the usual work up and column separation

Sources & evidence

ORD record
ord-1e5c6a2c1a59487eafdb0e0efac54ece
Source dataset
uspto-grants-1989_07
Patent number
US04849574

Linked notes

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