Sodium Hydroxide → HCID 23036317, compound

HRID 1721945Notes

Reaction equation

HRID 1721945 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1(C)C=CC(S([O:39][CH2:40][CH2:41][CH2:42][Cl:43])(=O)=O)=CC=1>C(#N)C.C1C=CC=CC=1>[Cl:43][CH2:42][CH2:41][CH2:40][O:39][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 16028TetrabutylammoniumHCID 68490alpha-HydroxyacetophenoneHCID 694343-Chloropropyl p-toluenesulfonate

Product 1

HCID 23036317HCID 23036317, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2 ml of 2-hydroxy-acetophenone were added with stirring to a mixture of 2.31 g of tetrabutylammonium acid sulfate, 20 ml of 50% sodium hydroxide solution, 40 ml of benzene and 20 ml of acetonitrile and after adding 8.26 of 3-chloro-propyl p-toluene sulfonate, the mixture was heated under an inert atmosphere at 80° C. for 17 hours. The decanted aqueous phase was extracted with benzene and the organic phase was washed with water, dried over a deshydrant, filtered and evaporated to dryness. The residue was chromatographed over silica and eluted with a 95-5 benzene-ethyl acetate mixture. Evaporation ofthe solvents yielded 3.38 g of 1-[2-{3-chloropropoxy}-phenyl]-ethanone.

Workup

  1. extractionThe decanted aqueous phase was extracted with benzene
  2. washthe organic phase was washed with water
  3. customdried over a deshydrant
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed over silica
  7. washeluted with a 95-5 benzene-ethyl acetate mixture
  8. customEvaporation ofthe solvents

Sources & evidence

ORD record
ord-dd604f2bf168483bad14b841bf70882c
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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