p-Toluenesulfonic acid → 2-(4'-Chloro-4-methylbiphenyl-3-yl)-5-[1,3]dioxan-2-ylmethylcyclohexane-1,3-dione

HRID 1027372Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH:15]3[C:20](=[O:21])[CH2:19][CH:18]([CH2:22][CH:23]=[O:24])[CH2:17][C:16]3=[O:25])[CH:9]=2)=[CH:4][CH:3]=1.[CH2:26](O)[CH2:27][CH2:28][OH:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH:15]3[C:16](=[O:25])[CH2:17][CH:18]([CH2:22][CH:23]4[O:29][CH2:28][CH2:27][CH2:26][O:24]4)[CH2:19][C:20]3=[O:21])[CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of [4-(4′-chloro-4-methylbiphenyl-3-yl)-3,5-dioxocyclohexyl]-acetaldehyde (0.080 g, 0.23 mmol) and propane-1,3-diol (0.021 g, 0.27 mmol) in anhydrous toluene (4 ml) is added a single crystal of para-toluenesulfonic acid and the mixture is stirred at 80° C. for 45 minutes. After cooling to room temperature the solution is concentrated in vacuo to afford a crude product which is purified by flash column chromatography on silica (ethyl acetate eluant) to afford 2-(4′-chloro-4-methylbiphenyl-3-yl)-5-[1,3]dioxan-2-ylmethylcyclohexane-1,3-dione as a white foam.

Workup

temperatureAfter cooling to room temperature the solution
concentrationis concentrated in vacuo
customto afford a crude product which
customis purified by flash column chromatography on silica (ethyl acetate eluant)

Sources & evidence

ORD record: ord-ad14e9cfdaa24fb594269a788a81ca62
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735322B2

Reaction notes

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