Potassium Carbonate → Methyl 3-chloro-4-isopropoxybenzoate

HRID 2059923Notes

Reaction equation

HRID 2059923 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 (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 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-2d192a8e52324367b3c0fa2291f705fb
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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