Water → HCID 11159836, compound

HRID 845367Notes

Reaction equation

HRID 845367 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7](O)=[CH:8][CH:9]=1)=[O:3].Br[CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-:17].[K+].[K+].O>CC(C)=O>[CH3:15][CH2:14][CH2:13][CH2:12][O:17][CH2:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 74694'-HydroxyacetophenoneHCID 8002Butyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 11159836HCID 11159836, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 4-hydroxyacetophenone (27.2 g, 0.2 mole), 1-bromobutane (41.8 g, 0.305 mole) and potassium carbonate (41.4 g, 0.3 mole) in acetone (400 ml) were heated under reflux for 48 hours. Water (200 ml) was then added and the mixture extracted with ethyl acetate (300 ml) and washed with water (2×150 ml). The organic solution was dried and evaporated under reduced pressure to give an orange liquid which solidified on cooling to give the product (38.0 g, 99%) which was used in the next reaction without further purification.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 48 hours
  3. extractionthe mixture extracted with ethyl acetate (300 ml)
  4. washwashed with water (2×150 ml)
  5. customThe organic solution was dried
  6. customevaporated under reduced pressure
  7. customto give an orange liquid which
  8. temperatureon cooling

Sources & evidence

ORD record
ord-74ef2fcf46f7442a9482577b65000aba
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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