Toluene → p-METHYLACETOPHENONE

HRID 1194580Notes

Reaction equation

HRID 1194580 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Li+].[C:7]1([CH3:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:14](Cl)(=[O:16])[CH3:15]>ClC(Cl)C>[CH3:13][C:7]1[CH:12]=[CH:11][C:10]([C:14]([CH3:15])=[O:16])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6367Acetyl chlorideHCID 433294Lithium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8500p-METHYLACETOPHENONE

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To an agitated mixture of aluminium chloride (20 g., 0.15 mole) and lithium chloride (3.18 g., 0.075 mole) and dichloroethane (20 ml) at -15° C. wash slowly added toluene (4.6 g., 0.05 mole) and acetyl chloride (3.93 g., 0.05 mole) in dichloroethane (10 ml). The reaction mixture was left at -15° C. for one hour then allowed to warm up to room temperature overnight. After working up as described in Example 1, the 4-methylacetophenone obtained (7.17 g.), had a 1H NMR estimated purity of about 95%. 1H NMR showed less than 2% ortho isomers.

Sources & evidence

ORD record
ord-6b9212c08e054f7f9612fe8859a6bc85
Source dataset
uspto-grants-1989_03
Patent number
US04814508

Reaction notes

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