Toluene → HCID 14537611, compound

HRID 329949Notes

Reaction equation

HRID 329949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.[C:18]1(C)C=CC=CC=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][CH3:14])=[CH2:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1140Toluene2×HCID 14537609HCID 14537609, compound

Product 1

HCID 14537611HCID 14537611, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

A suspension of 47.4 g (0.133 mol) of methyl-triphenylphosphonium bromide and 15.3 g (0.137 mol) of potassium tert.-butylate in 250 ml of absolute toluene is heated under reflux for 30 minutes under dry nitrogen. 25.3 g (0.1 mol) of 1-(4-chlorophenyl)-4,4-dimethyl-3-heptanone, dissolved in 10 ml of absolute toluene, are then added dropwise during the course of 5 minutes. The reaction mixture is heated under reflux for a further 15 hours, then cooled to room temperature, washed twice with water and concentrated under reduced pressure. The residue is taken up in ethyl acetate, cooled to 5° C. and the crop of crystals formed is filtered off by suction. The filtrate is concentrated and distilled under reduced pressure. 23 g (91.8% of theory) of 2-(4-chlorophenylethyl)-3,3-dimethyl-1-hexene are obtained in the form of a yellow oil of boiling point 85°-87° C./0.1 mbar. ##STR30##

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 minutes under dry nitrogen
  3. additionare then added dropwise during the course of 5 minutes
  4. temperatureThe reaction mixture is heated
  5. temperatureunder reflux for a further 15 hours
  6. washwashed twice with water
  7. concentrationconcentrated under reduced pressure
  8. temperaturecooled to 5° C.
  9. customthe crop of crystals formed
  10. filtrationis filtered off by suction
  11. concentrationThe filtrate is concentrated
  12. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-db45f6d838b74940a259c9db9ecbcac0
Source dataset
uspto-grants-1990_01
Patent number
US04894383

Reaction notes

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