Anisole → Cyclobutyl(4-methoxyphenyl)methanone

HRID 645337Notes

Reaction equation

HRID 645337 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]1([C:9]([OH:11])=O)[CH2:8][CH2:7][CH2:6]1.[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[N+](CC)([O-])=O>[CH:5]1([C:9]([C:15]2[CH:16]=[CH:17][C:12]([O:18][CH3:19])=[CH:13][CH:14]=2)=[O:11])[CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 19494Cyclobutanecarboxylic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13813654Cyclobutyl(4-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent2×

Procedure

A solution of AlCl3 (13.4 g) in nitroethane (25 ml) was added to a solution of cyclobutane carboxylic acid (10.0 g) and anisole (10.8 g) in nitroethane (75 ml) at 10° C. The mixture was stirred for 5 hours at room temperature, was than poured on ice and extracted with MTBE. The organic phase was washed with aqueous sodium hydroxide, water and brine, dried (MgSO4) and concentrated in vacuo. The essentially clean ketone (10.8 g) was used in the next step.

Workup

  1. additionthan poured on ice
  2. extractionextracted with MTBE
  3. washThe organic phase was washed with aqueous sodium hydroxide, water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3261a68a68b9411693b7b568306ab53e
Source dataset
uspto-grants-2010_04
Patent number
US07704942B2

Reaction notes

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