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

HRID 1768592

反応式

HRID 1768592 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 539440592-(1-Naphthylmethylene)glutaric acid収率 42.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-52bcf35c8f9a48ab9eaceb524530e261
出典データセット
uspto-grants-1995_01
特許番号
US05378690

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