Isopropyl iodide → Methyl 4-hydroxy-2-isopropoxybenzoate

HRID 1018958Notes

Reaction equation

HRID 1018958 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].I[CH:14]([CH3:16])[CH3:15]>C1C=CC=CC=1>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[OH:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:1][CH:14]([CH3:16])[CH3:15])[CH:11]=1

Participants

5

Reactant 2

HCID 6362Isopropyl iodide2×HCID 16523Methyl 2,4-Dihydroxybenzoate2×

Product 2

HCID 18398692Methyl 4-hydroxy-2-isopropoxybenzoateHCID 23244891Methyl 2-hydroxy-4-isopropoxybenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2,4-dihydroxybenzoate (5.4 g) and 2-iodopropane (10.2 g) in benzene (200 mL) was added Ag2CO3 and the mixture was heated in a 100° C. oil bath for 1 h. Additional methyl 2,4-dihydroxybenzoate (5 g) and 2-iodopropane (5 g) were added and the mixture was heated at 100° C. for another 2 h. After cooling, the mixture was filtered and concentrated. The residue was purified by flash chromatography eluted with 30:1 toluene/EtOAc to give 3 g of the title compound along with 1.2 g of isomer methyl 4-hydroxy-2-isopropoxybenzoate.

Workup

  1. temperaturethe mixture was heated at 100° C. for another 2 h
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluted with 30:1 toluene/EtOAc

Sources & evidence

ORD record
ord-41187ae6b6834580baafd2f54ae13165
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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