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

HRID 1987294Notes

Reaction equation

HRID 1987294 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+].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:9])[CH3:10])=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 7678PhenylacetoneHCID 77224-Methylbenzyl chlorideHCID 14797Potassium Hydroxide

Product 1

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

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

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-f5a4225dfc424ebc93743a584e8d02f2
Source dataset
uspto-grants-2009_06
Patent number
US07550489B2

Reaction notes

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