Ethylbenzene → 4'-Ethylbenzoin

HRID 375038

Reaction equation

HRID 375038 reaction equation
O.[C:2]1([C:8]([CH:10]=[O:11])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13]>ClC(Cl)C.[Ti](Cl)(Cl)(Cl)Cl>[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:10]([OH:11])[C:8](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=1)[CH3:13]

Participants

5

Reactant 2

HCID 7500EthylbenzeneHCID 12215922Glyoxal, phenyl-, hydrate

Product 1

HCID 153006894'-EthylbenzoinYield 74%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

Phenylglyoxal monohydrate (304 mg, 2 mM) and ethylbenzene (0.49 ml, 4 mM) were dissolved in dichloroethane (4 ml), titanium tetrachloride (0.33 ml, 3 mM) was added, and reacted at room temperature for 2 hours. The reaction mixture was extracted with ethylacetate, the extract was washed with saturated sodium hydrogen carbonate solution and brine, dried with sodium sulfate anhydrous, and then concentrated to obtain a yellow-colored oil. The oil was crystallized from a petroleum ether/diethylether to obtain 357.1 mg (74.0% yield) of 4'-ethylbenzoin.

Workup

  1. customreacted at room temperature for 2 hours
  2. extractionThe reaction mixture was extracted with ethylacetate
  3. washthe extract was washed with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried with sodium sulfate anhydrous
  5. concentrationconcentrated
  6. customto obtain a yellow-colored oil
  7. customThe oil was crystallized from a petroleum ether/diethylether

Sources & evidence

ORD record
ord-374784cfa61e419b83146e90f4f0eb8b
Source dataset
uspto-grants-1996_01
Patent number
US05484689

Linked notes

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