Acetone → HCID 22844417, compound

HRID 892673Notes

Reaction equation

HRID 892673 reaction equation
[CH2:1]([C@@H:3]1[C:8]([CH3:10])([CH3:9])[C@H:7]([CH:11]=O)[C:6]([CH3:13])=[CH:5][CH2:4]1)[CH3:2].[CH3:14][C:15]([CH3:17])=[O:16].CO[Na].CC(=O)C=C>C(O)C.CO>[CH2:1]([C@H:3]1[C:8]([CH3:10])([CH3:9])[C:7](/[CH:11]=[CH:14]/[C:15](=[O:16])[CH3:17])=[C:6]([CH3:13])[CH2:5][CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6570Methyl vinyl ketoneHCID 57294670HCID 57294670, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 22844417HCID 22844417, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

This compound was prepared by aldol condensation of 2 g (0.011 mol) of (+)-(1R,5S)-5-ethyl-2,6,6-trimethyl-2-cyclohexen-1-carbaldehyde (obtained according to example 4i.) with 2 ml (0.03 mol) of acetone, in 10 ml of ethanol. After adding 0.1 ml of a 30% solution of CH3ONa in methanol, the reaction was allowed to proceed for about 65 h. Following the usual treatment, 1.3 g of 95% pure mixture were obtained, containing 83% of the above-mentioned butenone, 13% of its α-trans isomer and 4% of its α-cis isomer.

Workup

  1. customwere obtained

Sources & evidence

ORD record
ord-78b2726e3119468884b95930392f9853
Source dataset
uspto-grants-1992_06
Patent number
US05118865

Reaction notes

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