Acetic Acid → HCID 20063336、化合物

HRID 1084454ノート

反応式

HRID 1084454 の反応式
C([O:3][C:4]([C:6]1(C(OCC)=O)[C:16](O)([CH:17]([CH3:19])[CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:7]1)=[O:5])C.C(O)(=O)C.Cl.C(=O)([O-])O.[Na+]>O>[CH:17]([C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:7][C:6]=1[C:4]([OH:5])=[O:3])([CH3:19])[CH3:18]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20063323HCID 20063323、化合物

生成物 1

HCID 20063336HCID 20063336、化合物収率 40%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A stirred mixture of crude 3,3-bis(ethoxycarbonyl)-4-hydroxy-4-isopropyl-3,4-dihydroisocoumarin (76 g), glacial acetic acid (500 ml) and concentrated hydrochloric acid (800 ml) was refluxed for 18 hours. The cooled mixture was added to ice/water (3500 ml) and the precipitated solid filtered off and washed with water to give an off-white solid. This was treated with a solution of sodium hydrogen carbonate (40 g) in water (400 ml) and the resultant solution was extracted with diethyl ether (150 ml). The aqueous phase was acidified to pH1 with concentrated hydrochloric acid and the white precipitate filtered off, washed with water and dried at 70° C. to give 4-isopropylisocoumarin-3-carboxylic acid (20.16 g) in the form of a white solid [Elemental analysis: C, 67.4; H, 5.2%; calculated: C, 67.2; H, 5.17%; NMR (in DMSO-d6): 1.45 (6H, d, J=8 Hz), 3.85 (1H, sept, J=8 Hz), 7.6-8.4 (4H, m)].

後処理

  1. temperaturewas refluxed for 18 hours
  2. filtrationthe precipitated solid filtered off
  3. washwashed with water
  4. customto give an off-white solid
  5. extractionthe resultant solution was extracted with diethyl ether (150 ml)
  6. filtrationthe white precipitate filtered off
  7. washwashed with water
  8. customdried at 70° C.

出典と根拠

ORDレコード
ord-7ecfebc3723645c8a8d71f83e2d8acdb
出典データセット
uspto-grants-1991_04
特許番号
US05004747

反応ノート

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