Potassium Carbonate → 3-(2-Hydroxymethyl-4-iodophenoxy)-3-methyl-2-butanone

HRID 2399307Notes

Reaction equation

HRID 2399307 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5].Br[C:12]([CH3:17])([CH3:16])[C:13](=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[OH:5][CH2:4][C:3]1[CH:6]=[C:7]([I:10])[CH:8]=[CH:9][C:2]=1[O:1][C:12]([CH3:17])([CH3:16])[C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3449113-Bromo-3-methyl-2-butanone2×HCID 125452592-(Hydroxymethyl)-4-iodophenol

Product 1

HCID 193870123-(2-Hydroxymethyl-4-iodophenoxy)-3-methyl-2-butanoneYield 104.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture containing 2-hydroxy-5-iodobenzyl alcohol (0.63 g, 0.00252 mol), 3-bromo-3-methyl-2-butanone (0.42 g, 0.00254 mol) and potassium carbonate (0.42 g, 0.00377 mol) in methyl ethyl ketone (7 ml) was heated at reflux for three hours. Then a further equivalent of 3-bromo-3-methyl-2-butanone (0.42 g, 0.00254 mol) was added. After heating at reflux for three hours, the cooled mixture was washed successively with water and aqueous sodium hydroxide solution, then extracted with ethyl acetate. The organic layer was evaporated to afford 0.88 g (100%) of crude 3-(2-hydroxymethyl-4-iodophenoxy)-3-methyl-2-butanone.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. temperatureAfter heating
  4. temperatureat reflux for three hours
  5. washthe cooled mixture was washed successively with water and aqueous sodium hydroxide solution
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-905f9d28c5ce4e8f94694c1069734f07
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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