Methacrylic Acid → HCID 71230785, compound

HRID 716473Notes

Reaction equation

HRID 716473 reaction equation
[C:1](O)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][CH:19]([CH3:21])[CH3:20])([CH3:10])([CH3:9])[CH3:8].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[CH2:18]([O:17][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][C:11]=1[C:7]([CH3:10])([CH3:9])[CH3:8])[C:1](=[O:5])[CH:2]([CH3:4])[CH2:3]2)[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 64764771HCID 64764771, compoundHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 71230785HCID 71230785, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 75.1 g (0.872 mol) of methacrylic acid and 90.0 g (0.436 mol) of 1-tert-butyl-2-isobutoxybenzene was added dropwise to Eaton's reagent (prepared from 119 g of P4O10 and 600 ml of MeSO3H) for 2 h at 50° C. The resulting mixture was stirred at 50° C. for 30 min, then cooled to room temperature, and poured into 1 liter of cold water. The crude product was extracted with 3×200 ml of dichloromethane. The organic extract was washed with aqueous K2CO3, dried over Na2SO4, and then passed through a pad of silica gel (40-63 um). The silica gel pad was additionally washed by 100 ml of dichloromethane. The combined elute was evaporated to dryness. The residue was distilled in vacuum, b.p. 155-170° C./5 mm Hg. The product was purified by flash chromatography on silica gel 60 (40-63 um; eluent: n-hexane-dichloromethane-ether=25:25:1, vol.) to give 91.9 g (76%) of the title indanone.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe crude product was extracted with 3×200 ml of dichloromethane
  3. extractionThe organic extract
  4. washwas washed with aqueous K2CO3
  5. dry with materialdried over Na2SO4
  6. washThe silica gel pad was additionally washed by 100 ml of dichloromethane
  7. washThe combined elute
  8. customwas evaporated to dryness
  9. distillationThe residue was distilled in vacuum, b.p. 155-170° C./5 mm Hg
  10. customThe product was purified by flash chromatography on silica gel 60 (40-63 um; eluent: n-hexane-dichloromethane-ether=25:25:1, vol.)

Sources & evidence

ORD record
ord-fac6591ddaa3450ea028f9096e85d38e
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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