Acetophenone → HCID 22153374, compound

HRID 845368Notes

Reaction equation

HRID 845368 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CCCCOC[C:16]([C:18]1[CH:23]=[CH:22]C=CC=1)=[O:17].CC(C)([O-])C.[K+].[C:30](=O)([O:34]CC)[O:31][CH2:32][CH3:33]>O.C1(C)C=CC=CC=1>[CH2:16]([O:17][C:7]1[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH2:2][C:30]([O:31][CH2:32][CH3:33])=[O:34])=[CH:5][CH:6]=1)[CH2:18][CH2:23][CH3:22]

Participants

7

Reactant 4

HCID 7410AcetophenoneHCID 7766Diethyl CarbonateHCID 11159836HCID 11159836, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22153374HCID 22153374, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

The acetophenone (9.6 g, 0.05 mole) from (d) was added to a suspension of potassium t-butoxide (9.0 g, 0.08 mole) in diethyl carbonate (24.0 g, 0.2 mole) at 75° C. over 10 minutes. Toluene (40 ml) was added to keep the suspension mobile and heating at 95° C. continued for 30 minutes. After cooling to 50° C., the suspension was poured into cold water (500 ml) and extracted with ethyl acetate (300 ml). The organic solution was dried and evaporated under reduced pressure to give the product (13.2 g, 95%) as a dark red liquid which was used in the next reaction without further purification.

Workup

  1. temperatureAfter cooling to 50° C.
  2. extractionextracted with ethyl acetate (300 ml)
  3. customThe organic solution was dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-54d3755ca6f34b0cbb047f7a75c38569
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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