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

HRID 1174079Notes

Reaction equation

HRID 1174079 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]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=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-one

Reagents, catalysts & solvents 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Procedure

A mixture of 1-tert-butyl-2-methoxybenzene (32.8 g, 0.2 mol) and methacrylic acid (21.5 g, 0.25 mol) was added at 60° C. to a well stirred Eaton reagent (55 g P2O5 and 280 ml of methanesulfonic acid). After 1 h of stirring the reaction mixture was cooled, poured into ice water, and extracted with benzene (3×200 ml). The combined organic layer was washed with water, aq. NaHCO3, dried over MgSO4, evaporated and distilled at 145-150° C./0.7 Torr. Yield 20 g (43%).

Workup

  1. temperaturewas cooled
  2. extractionextracted with benzene (3×200 ml)
  3. washThe combined organic layer was washed with water, aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. distillationdistilled at 145-150° C./0.7 Torr

Sources & evidence

ORD record
ord-464e3aaf06a8453bacbc15d1f1397e30
Source dataset
uspto-grants-2010_11
Patent number
US07834205B2

Reaction notes

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