Dichloromethane → 3-Octanoyloxy-2-(4'-methylphenyl)-5,5-dimethyl-2-cyclohexenone

HRID 370389Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10][C:9]2=[O:17])=[CH:4][CH:3]=1.[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(N(CC)CC)C.C(Cl)Cl>>[C:18]([O:17][C:9]1[CH2:10][C:11]([CH3:15])([CH3:16])[CH2:12][C:13](=[O:14])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8124Octanoyl chloride

HCID 8471Triethylamine

HCID 132597702-(4'-Methylphenyl)-5,5-dimethyl-1,3-cyclohexanedione

Product 1

HCID 202758213-Octanoyloxy-2-(4'-methylphenyl)-5,5-dimethyl-2-cyclohexenoneYield 71%

Procedure

Using the procedure described in Example III and starting with 3.00 g (0.0130 mol) of 2-(4'-methylphenyl)-5,5-dimethyl-1,3-cyclohexanedione, 1.59 g (0.0098 mol) of octanoyl chloride, 2.63 g (0.0260 mol) of triethylamine, and 30 mol of methylene chloride, 2.5 g (71% yield) of a clear, colorless oil was obtained as the desired product.

Sources & evidence

ORD record: ord-55dd89a8e8574dfead7a3b3ed5ff2bb6
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04526723

Reaction notes

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