Benzyltrimethylammonium hydroxide → 6-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acid

HRID 2163393노트

반응식

HRID 2163393 반응식
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][CH2:13][CH3:14])[CH2:2]1.[OH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:24][C:23]([C:25]([O:27]CC)=[O:26])=[CH:22][C:21](=[O:30])[C:20]=2[CH:31]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)C.O.CN(C)C=O>[OH:1][CH:3]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][CH3:14])[CH2:2][O:15][C:16]1[CH:17]=[CH:18][C:19]2[O:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][C:21](=[O:30])[C:20]=2[CH:31]=1

참가 물질

8

반응물 4

HCID 66854Benzyltrimethylammonium hydroxideHCID 516892Sodium BicarbonateHCID 6164644H-1-Benzopyran-2-carboxylic acid, 6-hydroxy-4-oxo-, ethyl esterHCID 123558511,2-Epoxy-3-(2-propylphenoxy)propane

생성물 1

HCID 130909986-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acid

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 19.2 parts of 1,2-epoxy-3-(2-propylphenoxy) propane, 23.4 parts of ethyl 6-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate and 0.1 parts of benzyl trimethylammonium hydroxide in 50 parts of dimethyl formamide was heated under reflux for 3 hours. The solvent was evaporated under reduced pressure and the oil remaining dissolved in ethyl acetate. The solution was washed with dilute sodium hydroxide and water, dried over magnesium sulphate, filtered and evaporated to leave an oil. The oil was dissolved in ethyl alcohol, 20.0 parts of sodium bicarbonate were added, and the mixture was boiled for 2 hours, during which time water was added and the ethyl alcohol allowed to boil off. The aqueous solution was washed with ethyl acetate and acidified with dilute hydrochloric acid to give a brown precipitate which was collected and crystallised twice from ethyl alcohol to yield 10.5 parts of 6-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acid, melting point 164°-166° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe oil remaining dissolved in ethyl acetate
  5. washThe solution was washed with dilute sodium hydroxide and water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto leave an oil
  10. additionwas added
  11. washThe aqueous solution was washed with ethyl acetate
  12. customto give a brown precipitate which
  13. customwas collected
  14. customcrystallised twice from ethyl alcohol

출처 및 근거

ORD 기록
ord-a2c87579d9314c07b9304a9cfdfd370d
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04133889

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