Potassium Carbonate → Methyl 3-chloro-4-isopropoxybenzoate

HRID 2383297Notes

Reaction equation

HRID 2383297 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].I[CH2:20][CH2:21][CH3:22]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:21]([CH3:22])[CH3:20])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 22597811Methyl 3-chloro-4-isopropoxybenzoateYield 104.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-chloro-4-hydroxybenzoate (available from Pfalz % Bauer, 50 g, 0.27 mole), K2CO3 (74 g, 0.54 mole) and iodopropane (29.5 ml, 0.23 mole) were stirred at room temperature in DMF (100 mL). After 18 h hours, the solvent was removed by evaporation under vacuum and the residue was chromatographed over a column of silica 60 in EtOAc/hexane (1:1) to give the title compound as an oil (55 g, 90%). 1H NMR (400 MHz, CDCl3) δ 8.05 (1H, d), 7.89 (1H, dd), 6.94 (1H, d), 4.60-4.72 (1H, m), 3.89 (3H, s), 1.41 (6H, d); m/z (API-ES) 229 [M+H]+.

Workup

  1. customthe solvent was removed by evaporation under vacuum
  2. customthe residue was chromatographed over a column of silica 60 in EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-36d748ad22d0491ab6af458d7ad6c1d0
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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