Toluene → 4-(4-Methylphenyl)-3-phenylbutan-2-one

HRID 133463Notes

Reaction equation

HRID 133463 reaction equation
[C:1]1([CH2:7][C:8]([CH3:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20](Cl)Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:9])[CH3:10])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 7678PhenylacetoneHCID 14797Potassium Hydroxide

Product 1

HCID 126157934-(4-Methylphenyl)-3-phenylbutan-2-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

1-Phenylacetone (200 mg, 1.49 mmol) was mixed with powdered potassium hydroxide (167 mg, 2.98 mmol) and tetra-n-butylammonium bromide (1 mol %, 5 mg) in a flask without solvent. This mixture was stirred at room temperature for 90 min. before the addition of 1-chloromethyl)-4-methylbenzene (198 μl, 1.49 mmol). The reaction mixture was then stirred overnight before diluting with water and CH2Cl2. The aqueous layer was separated and neutralized to pH 7 with 2N hydrochloric acid and extracted again into CH2Cl2. The combined organic washes were dried with MgSO4 and concentrated. The crude material was purified by column chromatography on silica gel eluting from 0-10% EtOAc/hexane to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.35 (t, J=7.0 Hz, 2H), 7.29 (t, J=7.4 Hz, 1H), 7.23 (d, J=7.1 Hz, 2H), 7.05 (d, 7.8 Hz, 2H), 6.98 (d, J=7.8 Hz, 2H), 3.94 (t, J=7.3 Hz, 1H), 3.43 (dd, J=13.9, 7.5 Hz, 1H), 2.91 (dd, J=14, 7.1 Hz, 1H), 2.32 (s, 3H), 2.08 (s, 3H). LC-MS: m/e 239 (M+H)+ (3.61 min).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted again into CH2Cl2
  3. dry with materialThe combined organic washes were dried with MgSO4
  4. concentrationconcentrated
  5. customThe crude material was purified by column chromatography on silica gel eluting from 0-10% EtOAc/hexane

Sources & evidence

ORD record
ord-fda724c4a901479cabdfd477a24e7fc3
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Reaction notes

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