Phthalaldehydic acid → t-Butyl 3-(2-carboxyphenyl)acrylate

HRID 1533260

反応式

HRID 1533260 の反応式
[Cl-].[C:2]([O:6][C:7]([CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[C:35]([C:38]1[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=1[CH:40]=O)([OH:37])=[O:36]>O1CCCC1>[C:35]([C:38]1[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=1[CH:40]=[CH:9][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:8])([OH:37])=[O:36]

参加物

5

反応物 3

HCID 8406Phthalaldehydic acidHCID 16211488(2-(tert-Butoxy)-2-oxoethyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 53853802t-Butyl 3-(2-carboxyphenyl)acrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of (t-butoxycarbonylmethyl)-triphenylphosphonium chloride (20.7 g) in tetrahydrofuran (200 ml) was added potassium t-butoxide (5.60 g) portionwise and the mixture was stirred for 30 minutes at ambient temperature. 2-Carboxybenzaldehyde was added to the mixture. After being stirred for 1 hour the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in 1N aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was acidified by conc. hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure to afford t-butyl 3-(2-carboxyphenyl)acrylate (8.3 g).

後処理

  1. stirringAfter being stirred for 1 hour the reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in 1N aqueous sodium hydroxide solution
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-99b38664f6b04ac9b4924ee3d4bd23bc
出典データセット
uspto-grants-2001_03
特許番号
US06207686B1

関連ノート

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