HCID 19937697, compound → 2-Phenyl-1-tetralone

HRID 36740Notes

Reaction equation

HRID 36740 reaction equation
[CH2:1]([Mg]Br)[CH3:2].Cl[CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1(C1C=CC=CC=1)[OH:16]>C1C=CC=CC=1>[C:2]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH:1]=[CH:8][CH:7]=[CH:6][CH:15]=1

Participants

4

Reactant 2

HCID 19937697HCID 19937697, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 3483282-Phenyl-1-tetraloneYield 187.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

Step C Add ethylmagnesium bromide (1.76 mL, 5.27 mmol, M in) dropwise to a 0° C. solution of 2-chloro-1-phenyl-1,2,3,4-tetrahydronaphth-1-ol (1.36 g, 5.27 mmol) in dry benzene (20 mL). Stir the solution at 0° C. for 30 min and heat to reflux for 5 hours. Cool the mixture to room temperature and quench with saturated NH4Cl (aqueous). Extract with ether, combine the ethereal extracts, wash with water and brine, dry over Na2SO4 and concentrate to provide 1.1 g (94%) of the title compound.

Workup

  1. temperatureheat
  2. temperatureto reflux for 5 hours
  3. temperatureCool the mixture to room temperature
  4. customquench with saturated NH4Cl (aqueous)
  5. extractionExtract with ether
  6. washwash with water and brine
  7. dry with materialdry over Na2SO4
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-a1ff33aa23844205b97f4101a245f871
Source dataset
uspto-grants-1995_05
Patent number
US05416118

Reaction notes

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