1,2,3,4-Tetramethylbenzene → 2',3',4',5'-Tetramethylbenzoin

HRID 375050Notes

Reaction equation

HRID 375050 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.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[C:14]=1[CH3:21]>ClC(Cl)C.[Ti](Cl)(Cl)(Cl)Cl>[CH3:19][C:16]1[C:15]([CH3:20])=[C:14]([CH3:21])[C:13]([CH3:12])=[CH:18][C:17]=1[CH:10]([OH:11])[C:8](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 102631,2,3,4-TetramethylbenzeneHCID 12215922Glyoxal, phenyl-, hydrate

Product 1

HCID 189940752',3',4',5'-TetramethylbenzoinYield 70.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

Phenylglyoxal monohydrate (304 mg, 2 mM) and 1,2,3,4-tetramethylbenzene (0.60 ml, 4 mM were dissolved in dichloroethane (5 ml), titanium tetrachloride (0.33 ml, 3 mM) was added, and reacted at room temperature for 10 minutes. Using the same procedure as in Example 1, 2',3',4',5'-tetramethylbenzoin was obtained (378.2 mg, 70.7% yield).

Workup

  1. customreacted at room temperature for 10 minutes

Sources & evidence

ORD record
ord-0e506425ac1548dcbb49ef5fc9ff1ca7
Source dataset
uspto-grants-1996_01
Patent number
US05484689

Reaction notes

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