Iodine → Ethyl 4-methoxy-3,5-dimethylbenzoate

HRID 864377ノート

反応式

HRID 864377 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[CH:3]=1.[Mg].II.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>O1CCCC1>[CH2:19]([O:18][C:16](=[O:17])[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[CH:3]=1)[CH3:20]

参加物

6

反応物 4

HCID 807IodineHCID 10928Ethyl chloroformateHCID 2786544-Bromo-2,6-dimethylanisoleHCID 5462224Magnesium

生成物 1

HCID 53404664Ethyl 4-methoxy-3,5-dimethylbenzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 4-bromo-2,6-dimethylanisole (PREPARATION 1, 12.98 g) in tetrahydrofuran (40 ml) is added drop by drop to a mixture of magnesium turnings (1.87 g) in tetrahydrofuran (5 ml). The Grignard reaction is initiated with iodine crystals. After the addition is complete, the mixture is refluxed for 2 hours. The Grignard reagent is cooled to about 10° and then a solution of ethyl chloroformate (7.5 ml) in tetrahydrofuran (40 ml) is added in a 2 minute period. The mixture is stirred for 45 minutes at ice-water temperature and then at 20°-25° for 2 hours. The reaction is quenched with a saturated solution of ammonium chloride and diluted with ether. The phases are separated, the organic phase is washed with water and then with saline, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound.

後処理

  1. customThe Grignard reaction
  2. additionAfter the addition
  3. temperaturethe mixture is refluxed for 2 hours
  4. customThe reaction is quenched with a saturated solution of ammonium chloride
  5. additiondiluted with ether
  6. customThe phases are separated
  7. washthe organic phase is washed with water
  8. dry with materialwith saline, dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-217bdb3ac8884d87a4cfc49d7a066f65
出典データセット
uspto-grants-1996_10
特許番号
US05563142

反応ノート

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