p-Toluenesulfonic acid monohydrate → 4-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 879086Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (0.0418 g, 0.10 mmol) in toluene (0.3 ml) is added p-toluenesulfonic acid monohydrate (0.019 g, 0.10 mmol). The mixture is then heated at 150° C. for 1 hour, after which it is allowed to cool to room temperature. The reaction mixture is poured into distilled water, dried over sodium sulfate, then concentrated in vacuo to afford 4-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

temperatureto cool to room temperature
additionThe reaction mixture is poured
distillationinto distilled water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ee91f4f900ec456a8903b11e189b1588
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987476B2

Reaction notes

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