Anisole → Methyl 8-(4-methoxyphenyl)-8-oxooctanoate

HRID 584388Notes

Reaction equation

HRID 584388 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6](=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].[C:18]1([O:24][CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH3:25][O:24][C:18]1[CH:23]=[CH:22][C:21]([C:6](=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 7519AnisoleHCID 4586585Methyl 8-chloro-8-oxooctanoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22344604Methyl 8-(4-methoxyphenyl)-8-oxooctanoateYield 88%

Procedure

Aluminium chloride (2.58 g) was added to a mixture of methyl 8-chloro-8-oxooctanoate (2.00 g) and anisole (5 ml) at 0° C. After stirring at room temperature for 14 hours, the reaction mixture was poured onto ice (50 g), stirred at room temperature for 1 hour and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl 8-(4-methoxyphenyl)-8-oxooctanoate (2.37 g, yield 88%) as crystals. The crystals were recrystallized from ethyl acetate-hexane to obtain colorless crystals. m.p. 57-58° C.

Workup

  1. additionthe reaction mixture was poured onto ice (50 g)
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef330e9e5ead4e838028d91efd0a5361
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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