Methacrylic Acid → 6-(tert-Butyl)-5-methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

HRID 716439Notes

Reaction equation

HRID 716439 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

4

Reactant 2

HCID 4093Methacrylic AcidHCID 270626tert-Butylanisole

Product 1

HCID 601502696-(tert-Butyl)-5-methoxy-2-methyl-2,3-dihydro-1H-inden-1-oneYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To Eaton's reagent obtained from 118 g of P4O10 and 600 ml of methanesulfonic acid a mixture of 70.3 g (0.428 mol) of 1-tert-butyl-2-methoxybenzene and 295.0 g (3.43 mol, 8 eqv.) of methacrylic acid was added for ca. 1 h at 50-55° C. The resulting mixture was stirred for 0.5 h at this temperature, then cooled to room temperature, and poured on a mixture of 1.5 liter of cold water and 2 kg of ice. After the ice melts, the precipitated crude 6-tert-butyl-5-methoxy-2-methylindan-1-one was filtered off and then washed with 2×100 ml of cold water. The crude product was dissolved in 500 ml of dichloromethane, and this solution was washed by aqueous K2CO3, dried over anhydrous K2CO3, and then evaporated on Rotavap. The residue was distilled in vacuum to give 70.6 g of crude 6-tert-butyl-5-methoxy-2-methylindan-1-one, b.p. 155-165° C./5 mm Hg. This product was dissolved in 200 ml of hot hexanes. Crystals precipitated from this solution at 5° C. were collected, washed by 50 ml of cold hexanes, and dried in vacuum. This procedure gave 64.1 g (65%) of the analytically pure substituted indanone.

Workup

  1. additionwas added for ca. 1 h at 50-55° C
  2. customthe precipitated crude 6-tert-butyl-5-methoxy-2-methylindan-1-one
  3. filtrationwas filtered off
  4. washwashed with 2×100 ml of cold water
  5. dissolutionThe crude product was dissolved in 500 ml of dichloromethane
  6. washthis solution was washed by aqueous K2CO3
  7. dry with materialdried over anhydrous K2CO3
  8. customevaporated on Rotavap
  9. distillationThe residue was distilled in vacuum

Sources & evidence

ORD record
ord-075018d1e8d9489c9483e88ff26117d5
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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