Iodoethane → Ethyl 5-tert-butyl-2-ethoxybenzoate

HRID 2425580Notes

Reaction equation

HRID 2425580 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[C:10]([C:14]1[CH:15]=[CH:16][C:17]([OH:23])=[C:18]([CH:22]=1)[C:19]([OH:21])=[O:20])([CH3:13])([CH3:12])[CH3:11].[CH3:24][C:25](=O)CC>>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([O:23][CH2:8][CH3:9])=[C:18]([CH:22]=1)[C:19]([O:21][CH2:24][CH3:25])=[O:20])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 852815-(1,1-Dimethylethyl)salicylic acid

Product 1

HCID 57732360Ethyl 5-tert-butyl-2-ethoxybenzoateYield 81%

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (9.4 g, 68.0 mmol) and iodoethane (3.3 mL, 41.3 mmol) were added to a stirred solution of 5-tert-butyl-2-hydroxy-benzoic acid (1.3 g, 6.8 mmol) in 2-butanone (50 mL). The resulting mixture was heated at 80° C. (oil bath) for 16 h and then allowed to cool. The solution was concentrated and redisolved in methylene chloride. The organic phase was washed with water, brine, and dried over anhydrous magnesium sulfate. The solids were filtered off, and the filtrate was concentrated. Purification of the crude residue by flash chromatography (silica gel, eluting with 5-10% ethyl acetate in hexanes) gave ethyl 5-tert-butyl-2-ethoxy-benzoate (1.2 g, 81%) as a yellow oil.

Workup

  1. temperatureto cool
  2. concentrationThe solution was concentrated
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solids were filtered off
  6. concentrationthe filtrate was concentrated
  7. customPurification of the crude residue
  8. washby flash chromatography (silica gel, eluting with 5-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fd45534f631a49ccb863837824119ab1
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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