Benzyl acetone → HCID 19792535, compound

HRID 1655508Notes

Reaction equation

[CH:1]1([C:7]([O:9]CC)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:12]1([CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH:1]1([C:7](=[O:9])[CH2:21][C:20](=[O:22])[CH2:19][CH2:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Reactant 2

HCID 17355Benzyl acetone

HCID 18686Ethyl cyclohexanoate2×

Product 1

HCID 19792535HCID 19792535, compound

Procedure

Using ethyl cyclohexane carboxylate (63 g, 0.4 mol) and 4-phenyl-2-butanone (20 g, 0.13 mol), the reaction was carried out in the same manner as described in Example 2, (1) and crude dark orange oil (23 g) was chromatographed on silica gel (Wako Gel C-200) eluting with n-hexane/ethyl acetate (100:1→100:2→100:3) to afford the title compound as a yellow oil which was an ca 3:17 mixture of Keto/Enol by the methylene singlet at δ3.55 ppm and the methine singlet at δ5.45 ppm in the 1HNMR spectrum; yield: 2.5 g.

Workup

customwas chromatographed on silica gel (Wako Gel C-200)
washeluting with n-hexane/ethyl acetate (100:1→100:2→100:3)

Sources & evidence

ORD record: ord-3d3b7008ea9244ae9a00103cd23bcf9d
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250669

Reaction notes

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