Acetone → 1-(4-Methylphenyl)propan-2-one

HRID 595364Notes

Reaction equation

HRID 595364 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.P.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:16][C:17]([CH3:19])=[O:18]>C(Cl)C=CC1C=CC=CC=1.[Pd]>[C:2]1([CH3:1])[CH:7]=[CH:6][C:5]([CH2:16][C:17](=[O:18])[CH3:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 78104-ChlorotolueneHCID 10796Cesium carbonateHCID 24404Phosphine

Product 1

HCID 1374281-(4-Methylphenyl)propan-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 131734589Palladium cinnamyl chlorideCatalyst

Procedure

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are p-methylphenyl chloride (127.0 mg, 1.0 mmol), palladium cinnamyl chloride (7.9 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino) henyldicyclohexyl)phosphine (24.3 mg, 0.060 mmol), Cs2CO3 (652.2 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 18 h. 1-(p-tolyl)-2-propanone (100.5 mg) was obtained with a yield of 68% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.19-7.05 (m, 4H, ArH), 3.66 (s, 2H, CH2), 2.34 (s, 3H, ArCH3), 2.15 (s, 3H, COCH3); 13C NMR (75 MHz, CDCl3) δ 206.7, 136.6, 131.1, 129.4, 129.2, 50.6, 29.1, 21.0; IR (neat) v (cm−1) 3023, 3004, 2922, 2857, 1714, 1615, 1514, 1417, 1356, 1229, 1158, 1040, 1023; MS (70 eV, EI) m/z (%): 149 (M++1, 3.90), 148 (M+, 31.26), 105 (100).

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 90° C.
  3. customfor 18 h

Sources & evidence

ORD record
ord-6a38ff32a0da428b8fede26af1a6fe9f
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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