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

HRID 2425580ノート

反応式

HRID 2425580 の反応式
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]

参加物

5

反応物 4

HCID 6340IodoethaneHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 852815-(1,1-Dimethylethyl)-2-hydroxybenzoic acid

生成物 1

HCID 57732360Ethyl 5-tert-butyl-2-ethoxybenzoate収率 81%

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fd45534f631a49ccb863837824119ab1
出典データセット
uspto-grants-2011_06
特許番号
US07964724B2

反応ノート

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