Carbon Dioxide → 3-(1,1-Dimethyldecyl)-4-methoxybenzoic acid

HRID 1651323ノート

反応式

HRID 1651323 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([C:10]([CH3:21])([CH3:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:3]=1.[Mg].II.[C:25](=[O:27])=[O:26].Cl>C1COCC1>[CH3:20][C:10]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[C:25]([OH:27])=[O:26])([CH3:21])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

参加物

7

反応物 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 807IodineHCID 5462224MagnesiumHCID 136335572-(1,1-Dimethyldecyl)-4-bromo anisole

生成物 1

HCID 136335583-(1,1-Dimethyldecyl)-4-methoxybenzoic acid収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

The 4-bromo-2-(1,1-dimethyldecyl) anisole (15.72 g, 44.2 mmoles) obtained in Example 11(a), above, is dissolved in THF (50 ml). This solution is slowly added to magnesium (1.18 g, 48.7 mmoles) and an iodine crystal, while being maintained at reflux by heating. Once the addition is complete, the reaction mixture is maintained at reflux for 30 minutes and then cooled to -40° C. 300 ml of THF are added and a stream of CO2 is passed therethrough for 2 hours. The reaction mixture is then poured into a solution of HCl (4N, 300 ml) and the product is extracted with ether (3×300 ml). The organic phase is washed with water until neutral, dried on MgSO4, and the solvents are evaporated. The residue is pulverized in isooctane to produce 7.25 g (51%. yield) of 3-(1,1-dimethyldecyl)-4-methoxy benzoic acid which melts at 112° C.

後処理

  1. temperatureat reflux
  2. temperatureby heating
  3. additionOnce the addition
  4. temperaturethe reaction mixture is maintained
  5. temperatureat reflux for 30 minutes
  6. extractionthe product is extracted with ether (3×300 ml)
  7. washThe organic phase is washed with water until neutral,
  8. customdried on MgSO4
  9. customthe solvents are evaporated

出典と根拠

ORDレコード
ord-337ce6b86b3d4fd49772f8f32bd98303
出典データセット
uspto-grants-1990_05
特許番号
US04927928

反応ノート

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