Acetone → HCID 66611398, compound

HRID 330835Notes

Reaction equation

HRID 330835 reaction equation
Br[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].CC(C)=O.[CH3:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:19]=1[I:25]>O>[CH3:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[C:22]([O:24][CH2:2][CH2:3][CH3:4])[CH:21]=[CH:20][C:19]=1[I:25]

Participants

6

Reactant 4

HCID 180AcetoneHCID 78401-Bromopropane2×HCID 11430Potassium Carbonate2×HCID 22349232Methyl 5-hydroxy-2-iodobenzoate

Product 1

HCID 66611398HCID 66611398, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.97 mL (32.7 mmol) 1-bromopropane and 299 mg (1.80 mmol) KI are added to a mixture of 3.39 g (24.5 mmol) K2CO3 and 200 mL acetone. The mixture is stirred for 30 min at reflux. Subsequently, 5.00 g (18.0 mmol) methyl-5-hydroxy-2-iodobenzoate are added and the resulting mixture is refluxed for 2 h. One additional equivalent of 1-bromopropane and of K2CO3 is added and refluxing is continued for 12 h. Water is added and the mixture is extracted with EtOAc. The organic layer is dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, heptane/EtOAc 100/0→60/40). The product is used without further characterization.

Workup

  1. temperatureat reflux
  2. temperaturethe resulting mixture is refluxed for 2 h
  3. temperaturerefluxing
  4. waitis continued for 12 h
  5. extractionthe mixture is extracted with EtOAc
  6. dry with materialThe organic layer is dried over sodium sulphate
  7. customthe solvent is removed in vacuo
  8. customThe crude product is purified by column chromatography (silica gel, heptane/EtOAc 100/0→60/40)

Sources & evidence

ORD record
ord-96c57ac3370d49e88fa044fe82c12f16
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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