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

HRID 1651323노트

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HRID 1651323 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-337ce6b86b3d4fd49772f8f32bd98303
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04927928

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