Cyclohexanone → Methyl cis-4-(1,3-pentadienyl)-1,5-dioxaspiro[5.5]undecane-2-acetate

HRID 974510Notes

Reaction equation

HRID 974510 reaction equation
[OH:1][CH:2]([CH2:8][CH:9]([OH:15])[CH:10]=[CH:11][CH:12]=[CH:13][CH3:14])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:10]([C@H:9]1[O:15][C:16]2([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:1][C@@H:2]([CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH2:8]1)=[CH:11][CH:12]=[CH:13][CH3:14]

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 53818818Methyl 3,5-dihydroxy-6,8-decadienoate

Product 1

HCID 86742960Methyl cis-4-(1,3-pentadienyl)-1,5-dioxaspiro[5.5]undecane-2-acetateYield 33.7%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Methyl 3,5-dihydroxy-6,8-decadienoate (7.6 g, 35.5 mmol) and p-toluenesulfonic acid (0.1 g) was added to cyclohexanone (10 g, 100 mmol) and stirred for 16 hours at ambient temperature. The yellow solution was loaded directly onto a silica gel column and the product eluted with diethyl ether:hexane (1:4). The appropriate fractions were combined to give 3.52 g (33.6%) of the title compound as a colorless oil.

Workup

  1. washthe product eluted with diethyl ether:hexane (1:4)

Sources & evidence

ORD record
ord-83f43ebcb78e4cfd9e276e2ec16eb0ce
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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