Water → 1-(2-Oxo-2-phenyl-ethyl)-3,4-dihydro-1H-naphthalen-2-one

HRID 1579877Notes

Reaction equation

HRID 1579877 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].C1(C)C=CC=CC=1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][C:19]=1N1CCCC1.[OH2:33]>>[CH2:1]([CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][C:19]1=[O:33])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 6259Phenacyl bromideHCID 888891-(3,4-Dihydro-2-naphthyl)pyrrolidine

Product 1

HCID 122703441-(2-Oxo-2-phenyl-ethyl)-3,4-dihydro-1H-naphthalen-2-one

Procedure

A solution of 20 g. (0.1 mole) of phenacyl bromide and 65 ml. of toluene was added during 30 minutes to a boiling, stirred solution of 20 g. (0.1 mole) of 1-(3,4-dihydro-2-naphthyl)pyrrolidine and 50 ml. of toluene. The mixture was heated under reflux for 3 hours, diluted with 50 ml. of water, refluxed for 4 hours and cooled. The layers were separated, the aqueous phase was extracted with benzene, and the organic solution was dried and concentrated to an oil. Crystallization from 30°-60°-petroleum ether-ether gave 16.7 g. (63%) of tan crystals, m.p. 48°-52°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. additiondiluted with 50 ml
  4. temperaturecooled
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with benzene
  7. customthe organic solution was dried
  8. concentrationconcentrated to an oil
  9. customCrystallization from 30°-60°-petroleum ether-ether
  10. customgave 16.7 g

Sources & evidence

ORD record
ord-c246363108d94e6f8c78cb459bdfde90
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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