Toluene → HCID 14328582, compound

HRID 1087695Notes

Reaction equation

HRID 1087695 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])[CH:12]([CH3:14])[CH3:13])=[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])[CH:12]([CH3:14])[CH3:13])=[CH2:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 14328581HCID 14328581, compound

Product 1

HCID 14328582HCID 14328582, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

A suspension of 47.4 g (0.133 mol) of methyltriphenyl-phosphonium bromide and 15.3 g (0.137 mol) of potassium tert.-butylate in 250 ml of absolute toluene is heated under reflux under dry nitrogen 25.2 g (0.1 mol) of 1-(4-chlorophenyl)-4,4,5-trimethyl-hexan-3-one are introduced over 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 with suction. The filtrate is concentrated and distilled under reduced pressure. 14.5 g (58% of theory) of 2-(4-chlorophenylethyl)-3,3,4-trimethyl-pent-1-ene are obtained in the form of a yellow oil of boiling point 88°-90° C./0.1 mbar. ##STR22##

Workup

  1. temperatureis heated
  2. additionare introduced over the course of 5 minutes The reaction mixture
  3. temperatureis heated
  4. temperatureunder reflux for a further 15 hours
  5. washwashed twice with water
  6. concentrationconcentrated under reduced pressure The residue
  7. temperaturecooled to 5° C.
  8. customthe crop of crystals formed
  9. filtrationis filtered off with suction
  10. concentrationThe filtrate is concentrated
  11. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-16f4d3d98d204e3ba67cdc617d19d631
Source dataset
uspto-grants-1990_10
Patent number
US04960453

Reaction notes

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