Acetic Acid → HCID 20063336, 화합물

HRID 1084454노트

반응식

HRID 1084454 반응식
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]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20063323HCID 20063323, 화합물

생성물 1

HCID 20063336HCID 20063336, 화합물수율 40%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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)].

후처리

  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.

출처 및 근거

ORD 기록
ord-7ecfebc3723645c8a8d71f83e2d8acdb
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05004747

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