Acetone → 1-(2,6-Dimethylphenyl)propan-2-one

HRID 595363

Reaction equation

HRID 595363 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1Cl.P.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][C:18]([CH3:20])=[O:19]>C(Cl)C=CC1C=CC=CC=1.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:17][C:18](=[O:19])[CH3:20]

Participants

6

Reactant 4

HCID 180AcetoneHCID 10796Cesium carbonateHCID 24404PhosphineHCID 328851-Chloro-2,6-dimethylbenzene

Product 1

HCID 135084401-(2,6-Dimethylphenyl)propan-2-oneYield 84%

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 2,6-dimethylphenyl chloride (142.4 mg, 1.0 mmol), palladium cinnamyl chloride (7.8 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyldicyclohexyl)phosphine (24.4 mg, 0.060 mmol), Cs2CO3 (651.9 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 22 h. 1-(2′,6′-Dimethylphenyl)-2-propanone (138.4 mg) was obtained with a yield of 84% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.15-7.03 (m, 3H, ArH), 3.79 (s, 2H, CH2), 2.27 (s, 6H, 2×ArCH3), 2.17 (s, 3H, COCH3); 13C NMR (75 MHz, CDCl3) δ 206.2, 136.7, 132.1, 128.1, 126.9, 45.0, 29.2, 20.2; IR (neat) v (cm−1) 3021, 2922, 2867, 1715, 1589, 1470, 1446, 1415, 1379, 1357, 1317, 1223, 1158, 1095, 1053, 1031; MS (70 eV, EI) m/z (%): 163 (M++1, 3.30), 162 (M+, 27.85), 119 (100); HRMS calcd for C11H14O (M+): 162.1045. Found: 162.1046.

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 90° C.
  3. customfor 22 h

Sources & evidence

ORD record
ord-747658f32fb64e5c92573819e5e5a6f8
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Linked notes

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