Iodoethane → HCID 68872281, compound

HRID 2105842Notes

Reaction equation

HRID 2105842 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[CH3:10][S:11][C:12]1[CH:13]=[CH:14][C:15]([OH:21])=[C:16]([CH:20]=1)[C:17]([OH:19])=[O:18].[CH3:22][C:23](=O)CC>>[CH3:10][S:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:8][CH3:9])=[C:16]([CH:20]=1)[C:17]([O:19][CH2:22][CH3:23])=[O:18]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 597283Benzoic acid, 2-hydroxy-5-(methylthio)-

Product 1

HCID 68872281HCID 68872281, compoundYield 85%

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (22.0 g, 159 mmol) and iodoethane (9.0 mL, 112 mmol) were added to a stirred solution of 5-methylthio-2-hydroxy-benzoic acid (5.00 g, 27 mmol) in 2-butanone (125 mL). The resulting mixture was heated in an oil bath (80° C.) for 16 h and then allowed to cool. The solution was concentrated and redissolved in methylene chloride. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with 5-15% ethyl acetate in hexanes) gave ethyl 5-methylthio-2-ethoxybenzoate as a yellow oil (5.5 g, 85%).

Workup

  1. temperatureto cool
  2. concentrationThe solution was concentrated
  3. dissolutionredissolved in methylene chloride
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customPurification of the crude residue
  8. washby flash column chromatography (silica gel, eluting with 5-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e80ffdfa2ce34332a8efbce4d8da8540
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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