Diethyl Ether → 1-[2,4-Dimethoxy-3-(3-phenylpropyl)phenyl]ethanone

HRID 2210076Notes

Reaction equation

HRID 2210076 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20](Cl)(=[O:22])[CH3:21].[Cl-].[Al+3].[Cl-].[Cl-].CCOCC>ClCCl>[CH3:10][O:9][C:5]1[C:4]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:20](=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 193799151,3-Dimethoxy-2-(3-phenylpropyl)benzene

Product 1

HCID 193799231-[2,4-Dimethoxy-3-(3-phenylpropyl)phenyl]ethanoneYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 15.28 g (59.6 mmol) of 1,3-dimethoxy-2-(3-phenylpropyl)benzene from the preceding example, and 4.68 g (59.6 mmol) of acetyl chloride, in 306 mL of dichloromethane was stirred at -5° to 0° C. and 7.95 g (59.6 mmol) of aluminum chloride was added. The resulting mixture was stirred at -5° to 0° C. for 2 hr and then allowed to warm to room temperature before being poured onto ice. Work-up with ether in the usual manner gave a product which was chromatographed on silica gel. Elution with 7:3 hexane-ether afforded 10.0 g (56.3%) of the title compound as a pale-yellow oil.

Workup

  1. customwas stirred at -5° to 0° C.
  2. additionbefore being poured onto ice
  3. customgave a product which
  4. customwas chromatographed on silica gel
  5. washElution with 7:3 hexane-ether

Sources & evidence

ORD record
ord-e08c8aed655f496ca69084fd87f1ea3c
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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