Dimethyl dicarbonate → 2,3,3',4'-Tetramethylbenzophenone

HRID 881778Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:16](O)=[O:17].C(OC(OC)=O)(OC)=O.C(=O)([O-])[O-].[K+].[K+]>[Pd].O1CCOCC1.O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:16]([C:15]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:13]([CH3:12])[CH:14]=1)=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 250 ml 3-necked round-bottom flask, 2,3-dimethylphenylboronic acid (3.6 g, 24 mmol), 3,4-dimethylbenzoic acid (3.0 g, 20 mmol), a selected palladium catalyst (0.6 mmol), dimethyl dicarbonate (2.7 g, 30 mmol) and potassium carbonate (6.22 g, 45 mmol) were mixed with 150 ml of dry dioxane. The reaction mixture was heated at 80° C. overnight to become a viscous reaction mixture. 20 ml of water was added to dissolve the heterogeneous reaction mixture, and dioxane was evaporated to dryness. The aqueous solution as extracted with 20 ml of ethyl acetate, dried over anhydrous magnesium sulfate and then evaporated to dryness. The crude product was purified by silica gel column chromatography eluted by hexane/ethyl acetate=20/80 to afford 2.0 g (33%) of the product.

Workup

customwas evaporated to dryness
extractionThe aqueous solution as extracted with 20 ml of ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
customevaporated to dryness
customThe crude product was purified by silica gel column chromatography
washeluted by hexane/ethyl acetate=20/80

Sources & evidence

ORD record: ord-6222a29006884ed5b93c4c039663b1f7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993710B1

Reaction notes

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