3-Chloro-2-methyl-1-propene → HCID 22159646, compound

HRID 1089607Notes

Reaction equation

HRID 1089607 reaction equation
[OH-].[Na+].N[C@H:4]([C:16](O)=O)[CH2:5]C1C=C2C(C=CC=C2)=CC=1.[CH3:19][C:20]([CH:22]([CH3:24])[CH3:23])=[O:21].[CH2:25](Cl)C(=C)C>O>[CH3:23][C:22]([CH3:25])([CH2:24][C:4]([CH3:16])=[CH2:5])[C:20](=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 112513-Methyl-2-butanoneHCID 14798Sodium HydroxideHCID 1859152-Naphthylalanine

Product 1

HCID 22159646HCID 22159646, compoundYield 569.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

93 g of NaOH, 12 g of Nal and 6.8 g of Emkapol 400 (polyethyleneglycol) were charged into a 1 l three-neck flask. 100 g of methylisopropyl ketone were added and, at 50°, 290 g of methallyl chloride. The mixture was heated to reflux for 4 h and then hydrolysed with 200 ml of water. The reaction product was washed to neutrality and distilled to provide 69.6 g of raw product (B. p. 56°-65°/5.0×103Pa). Distillation of this raw product on a Widmer column gave 44.5 g of the desired ketone.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. washThe reaction product was washed to neutrality
  4. distillationdistilled
  5. customto provide 69.6 g of raw product (B. p. 56°-65°/5.0×103Pa)
  6. distillationDistillation of this raw product on a Widmer column

Sources & evidence

ORD record
ord-80e779dc02a545ceac2b2df2244efbb2
Source dataset
uspto-grants-1990_10
Patent number
US04967033

Reaction notes

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