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

HRID 1973465Notes

Reaction equation

HRID 1973465 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

20 g (0.1 mole) of phenacyl bromide and 65 ml. of toluene are added dropwise during 30 minutes to a refluxing stirred solution of 20 g (0.1 mole) of 1-(3,4-dihydro-2-napthyl)pyrrolidine and 50 ml. of toluene. The mixture is heated under reflux for 3 hours, diluted with 50 ml. of water, refluxed for 4 hours and cooled. The layers separate, the aqueous phase is extracted with benzene, the organic solution is dried and concentrated to an oil. The oil is crystallized from a 30°-60° petroleum ether-ether mixture to give 1-phenacyl-2-tetralone as tan crystals, m.p. 48°-52° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. additiondiluted with 50 ml
  4. temperaturecooled
  5. customThe layers separate
  6. extractionthe aqueous phase is extracted with benzene
  7. customthe organic solution is dried
  8. concentrationconcentrated to an oil
  9. customThe oil is crystallized from a 30°-60° petroleum ether-ether mixture

Sources & evidence

ORD record
ord-71fd94696f5f44f5aa68a5a5d8f00c47
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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