Iodoethane → HCID 57554728, compound

HRID 2425583Notes

Reaction equation

HRID 2425583 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[OH:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1.[CH3:21][C:22](=O)CC>>[CH2:21]([O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]([O:20][CH2:8][CH3:9])=[O:19])[CH:14]=[CH:15][CH:16]=1)[CH3:22]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 57554728HCID 57554728, compoundYield 78%

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (65.3 g, 473 mmol) and iodoethane (25.5 mL, 324 mmol) were added to a stirred solution of 3-hydroxyphenylacetic acid (12.0 g, 79 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 mixture was concentrated and methylene chloride was added. The organic layer was washed with water, brine, and dried over anhydrous magnesium sulfate. The solids were filtered off, and the filtrate was concentrated to give ethyl 3-ethoxyphenylacetate (12.7 g, 78%) as a clear oil.

Workup

  1. temperatureto cool
  2. concentrationThe mixture was concentrated
  3. additionmethylene chloride was added
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solids were filtered off
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7b0da912631449a8909c3042f709a93c
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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