Benzoic Acid → Ethyl cyclopropylideneacetate

HRID 1920571Notes

Reaction equation

HRID 1920571 reaction equation
C(O[C:4]1(O[Si](C)(C)C)[CH2:6][CH2:5]1)C.C1(P(=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:4]1(=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilane

Product 1

HCID 11040705Ethyl cyclopropylideneacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 38.49 g (220.80 mmol) of [(1-ethoxycyclopropyl)oxy](trimethyl)silane, 100.0 g (287.04 mmol) of ethyl (triphenylphosphoranylidene)acetate and 3.51 g (28.70 mmol) of benzoic acid in 600 ml of toluene is stirred at a bath temperature of 90° C. for 18 hours. After cooling, the mixture is poured onto 800 g of silica gel 60 and eluted successively with in each case 3 liters of petroleum ether 40-60 and dichloromethane. The dichloromethane eluate is, after removal of the solvent, distilled at 160° C. and 14 mbar in a kugelrohr. This gives 17.95 g (64% of theory) of the title compound as a colorless liquid.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured onto 800 g of silica gel 60
  3. washeluted successively with in each case 3 liters of petroleum ether 40-60 and dichloromethane
  4. customafter removal of the solvent
  5. distillationdistilled at 160° C.

Sources & evidence

ORD record
ord-649bd9cf2f494c0480d63d8fb0fe56c5
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

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