Isopropyl iodide → Methyl 3-chloro-4-isopropoxybenzoate

HRID 2192462Notes

Reaction equation

HRID 2192462 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[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:20]([CH3:22])[CH3:21])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 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; available from Alfa Aesar), potassium carbonate (74 g, 0.54 mole) and 2-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 eluting with ethyl acetate/hexane (1:1) to give the title compound as an oil (55 g). MS: m/z (API-ES) 229 [MH+]; 1H NMR (400 MHz, CDCl3) δ (inter alia) 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).

Workup

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

Sources & evidence

ORD record
ord-a5c3da3c7e3c41beaf02bc078074cb72
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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