1-Naphthaldehyde → 2-(1-Naphthylmethylene)glutaric acid

HRID 1768592

반응식

HRID 1768592 반응식
[H-].[Na+].[C:3]([O:12]C)(=[O:11])[CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=[O:8].[C:14]1([CH:24]=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CO>[C:14]1([CH:24]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[C:3]([OH:12])=[O:11])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 61951-NaphthaldehydeHCID 14242Dimethyl GlutarateHCID 14798Sodium HydroxideHCID 24758Sodium hydride

생성물 1

HCID 539440592-(1-Naphthylmethylene)glutaric acid수율 42.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

8.17 g (0.19 mole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, with ice-cooling, to a solution of 25 g (0.16 mole) of dimethyl glutarate and 23.4 g (0.16 mole) of 1-naphthaldehyde dissolved in 200 ml of anhydrous methanol. The mixture was heated under reflux for 30 minutes, after which 190 ml (0.19 mole) of a 1N aqueous solution of sodium hydroxide were added and the mixture was heated under reflux for a further 1 hour. The solvent was then removed by distillation under reduced pressure, and the residue was mixed with water and then washed with diethyl ether. The aqueous layer was acidified and extracted with diethyl ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then diisopropyl ether was added to the residue to precipitate crystals, which were collected by filtration to give 18.5 g of 2-(1 -naphthylmethylene)glutaric acid.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 1 hour
  5. customThe solvent was then removed by distillation under reduced pressure
  6. additionthe residue was mixed with water
  7. washwashed with diethyl ether
  8. extractionextracted with diethyl ether
  9. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. additiondiisopropyl ether was added to the residue
  13. customto precipitate crystals, which
  14. filtrationwere collected by filtration

출처 및 근거

ORD 기록
ord-52bcf35c8f9a48ab9eaceb524530e261
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05378690

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