Isopropyl iodide → Methyl 3-chloro-4-isopropoxybenzoate

HRID 650954Notes

Reaction equation

HRID 650954 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].C(OCC)(=O)C>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

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 22597811Methyl 3-chloro-4-isopropoxybenzoateYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Methyl 3-chloro-4-hydroxybenzoate (5 g, 26.8 mmol) in DMF (45 ml) was treated with potassium carbonate (7.41 g, 53.6 mmol), 2-iodopropane (3.85 ml, 40.2 mmol) and then stirred at 25° C. for 18 h. Work-up with ethyl acetate gave the title compound (6.1 g).

Sources & evidence

ORD record
ord-b0fe985c95f7400aae4821a4b5d1a689
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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