Methacrylic Acid → 6-(tert-Butyl)-5-methoxy-2-methyl-2,3-dihydro-1H-inden-1-one
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[C:13](O)(=[O:17])[C:14]([CH3:16])=[CH2:15]>O>[C:1]([C:5]1[CH:10]=[C:9]2[C:8]([CH2:15][CH:14]([CH3:16])[C:13]2=[O:17])=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To an Eaton's reagent obtained from 110 g of P4O10 and 560 ml of methanesulfonic acid a mixture of 65.6 g (0.399 mol) of 1-tert-butyl-2-methoxybenzene and 43.0 g (0.50 mol) of methacrylic acid was added for ca. 1 h at 50-55° C. The resulting mixture was stirred for 1 h at this temperature, then cooled to room temperature, and poured on a mixture of 1 liter of cold water and 1 kg of ice. The crude product was extracted with 3×500 ml of dichloromethane. The combined organic extract was washed by aqueous K2CO3 and then evaporated to dryness. Fractional rectification of the residue gave 64.9 g of yellowish oil which crystallizes at room temperature. On the evidence of NMR spectroscopy, this product includes ca. 90% of the target material. Further on, this product was dissolved in 180 ml of hot hexanes. Crystals precipitated from this solution at room temperature were collected, washed by 100 ml of cold hexanes, and dried in vacuum. This procedure gave 39.6 g (43%) of the analytically pure substituted indanone.
Workup
- additionwas added for ca. 1 h at 50-55° C
- extractionThe crude product was extracted with 3×500 ml of dichloromethane
- extractionThe combined organic extract
- washwas washed by aqueous K2CO3
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-5db16dbc5b8c44ee9ae8ac901db4986b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187583B2
Reaction notes
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