Phenylglyoxal → 4'-n-Octylbenzoin

HRID 1382501Notes

Reaction equation

HRID 1382501 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl-].[Al+3].[Cl-].[Cl-].[C:19]1([C:25]([CH:27]=[O:28])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=S)=S>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH:27]([OH:28])[C:25](=[O:26])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 14090PhenylglyoxalHCID 16607OctylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137424104'-n-Octylbenzoin

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Conditions

Temperature
0 °C

Procedure

57.0 g (0.30 mole) of n-octylbenzene are dissolved in 800 ml of carbon disulfide, the solution is cooled to 0° C., 66.5 g (0.50 mole) of aluminum chloride are added, and a solution of 40.0 g (0.30 mole) of phenylglyoxal and 50 ml of carbon disulfide are added dropwise at from 5° to 10° C., while stirring vigorously. The yellow to orange reaction mixture is stirred for a further 15 hours without being cooled, after which it is poured carefully onto 1 l of semiconcentrated ice-cold hydrochloric acid, and the mixture is stirred thoroughly. The phases are separated, the organic phase is extracted by shaking with 300 ml of water, the aqueous phases are extracted with 300 ml of methylene chloride, and the combined organic phases are dried over sodium sulfate. The solution is filtered and the solvent is distilled off to give 75.0 g (=77% of theory) of crude product which has a melting range of 85°-89° C. and is 95% pure according to gas chromatography. Recrystallization from methanol gives analytically pure 4'-n-octylbenzoin.

Workup

  1. stirringThe yellow to orange reaction mixture is stirred for a further 15 hours
  2. temperaturewithout being cooled
  3. stirringthe mixture is stirred thoroughly
  4. customThe phases are separated
  5. extractionthe organic phase is extracted
  6. stirringby shaking with 300 ml of water
  7. extractionthe aqueous phases are extracted with 300 ml of methylene chloride
  8. dry with materialthe combined organic phases are dried over sodium sulfate
  9. filtrationThe solution is filtered
  10. distillationthe solvent is distilled off
  11. customto give 75.0 g (=77% of theory) of crude product which
  12. customRecrystallization from methanol

Sources & evidence

ORD record
ord-4bb8b3f580ed432a89f636d0bf30115f
Source dataset
uspto-grants-1989_02
Patent number
US04806664

Reaction notes

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