Potassium Carbonate → Methyl 4-methoxy-3-[(2-oxocyclopentyl)oxy]benzoate

HRID 1422034Notes

Reaction equation

HRID 1422034 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl[CH:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26]>CN(C=O)C>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[O:1][CH:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127512-ChlorocyclopentanoneHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 23296066Methyl 4-methoxy-3-[(2-oxocyclopentyl)oxy]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

23.8 g of methyl 3-hydroxy-4-methoxybenzoate are dissolved in 200 ml of anhydrous DMF and the solution is treated with 35 g of potassium carbonate (ground) and 13 ml of 2-chlorocyclopentanone. The mixture is stirred at 60° C. for 3 h, then the solid is filtered off with suction and the filtrate is concentrated in vacuo. The residue is chromatographed on a silica gel column using ethyl acetate/petroleum ether (4:6). The chromatographically pure fractions are combined, concentrated and dried in a high vacuum. 24.3 g of the title compound are obtained as a pale yellow oil.

Workup

  1. filtrationthe solid is filtered off with suction
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is chromatographed on a silica gel column
  4. concentrationconcentrated
  5. customdried in a high vacuum

Sources & evidence

ORD record
ord-0b5bff13e90c42ea8159475a12d1ce89
Source dataset
uspto-grants-2000_06
Patent number
US06080782

Reaction notes

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