Toluene → HCID 10987424, compound

HRID 1197719Notes

Reaction equation

HRID 1197719 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][CH:6]1[CH2:11][C:10](=[O:12])[O:9][C:7]1=[O:8].[C:13]1([CH3:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:19][C:13]1[CH:18]=[CH:17][C:16]([C:10]([CH2:11][CH:6]([CH3:5])[C:7]([OH:9])=[O:8])=[O:12])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 20051Methylsuccinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10987424HCID 10987424, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Aluminium trichloride (50.7 g, 0.38 mol) is added, portionwise, over 15 min, to a solution of methylsuccinic anhydride (20 g, 0.175 mol), toluene (32.3 g, 0.35 mol) and nitrobenzene (100 ml). The reaction mixture is stirred for 3 hours and then warmed to 80° C. for half an hour. On cooling, it is quenched with water (75 ml) and then conc HCl (30 ml). The solid ppt. is filtered, dissolved in Na2CO3 solution, washed with CH2Cl2, re-acidified and the product filtered to yield 23.4 g of 3-(4-methylbenzoyl)-2-methyl-propionic acid as a white solid, m.p. 168°-170°.

Workup

  1. temperatureOn cooling
  2. customit is quenched with water (75 ml)
  3. filtrationis filtered
  4. dissolutiondissolved in Na2CO3 solution
  5. washwashed with CH2Cl2
  6. filtrationre-acidified and the product filtered

Sources & evidence

ORD record
ord-f30ff361b3f046b99d80c60ef69044e0
Source dataset
uspto-grants-1994_01
Patent number
US05277709

Reaction notes

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