1-Chloro-3-methyl-2-butene → HCID 20439306, compound

HRID 1995870Notes

Reaction equation

HRID 1995870 reaction equation
[OH-].[Na+].[CH2:3]([C:10]([CH2:12][CH3:13])=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:14](Cl)[CH:15]=[C:16]([CH3:18])[CH3:17]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[CH3:17][C:16](=[CH:15][CH2:14][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10](=[O:11])[CH2:12][CH3:13])[CH3:18]

Participants

5

Reactant 3

HCID 104291-Chloro-3-methyl-2-buteneHCID 138791-Phenyl-2-butanoneHCID 14798Sodium Hydroxide

Product 1

HCID 20439306HCID 20439306, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 5974Hexadecyltrimethylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

192 g (2.4 mol) of 50% sodium hydroxide and 6 g of hexadecyl-trimethylammonium bromide are placed in a 2-liter flask provided with a thermometer, stirrer and reflux condenser and there is then added dropwise while stirring within 0.5 hour a mixture of 296 g (2 mol) of ethyl benzyl ketone and 251 g (2.4 mol) of prenyl chloride. The mixture is warmed to 60° C. and stirred for 3 hours. The mixture is left to cool and 500 ml of ice/water are added thereto. The mixture is extracted four times with ether and washed neutral with water. The phase separation can be facilitated by the addition of a small amount of alcohol. After drying over sodium sulphate, the ether is evaporated and a fractional distillation is then carried out. There are thus obtained 224 g of 2-methyl-5-phenyl-oct-2-en-6-one of boiling point 106° C./3 mmHg; nD20 =1.5092-88; yield 75%.

Workup

  1. customprovided with a thermometer, stirrer
  2. temperaturereflux condenser
  3. additionthere is then added dropwise
  4. stirringstirred for 3 hours
  5. waitThe mixture is left
  6. temperatureto cool
  7. extractionThe mixture is extracted four times with ether
  8. washwashed neutral with water
  9. customThe phase separation
  10. additioncan be facilitated by the addition of a small amount of alcohol
  11. dry with materialAfter drying over sodium sulphate
  12. customthe ether is evaporated
  13. distillationa fractional distillation

Sources & evidence

ORD record
ord-373a6d5ca5e642fc87bf3b267873b2a4
Source dataset
uspto-grants-1983_09
Patent number
US04406828

Reaction notes

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