Ethylene Glycol → 5-Benzyloxy-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran-4-carboxylic acid

HRID 1607463노트

반응식

HRID 1607463 반응식
[CH2:1]([O:8][C:9]1[C:14]2C(C#N)[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:32].[K+].[CH2:34]([OH:37])[CH2:35]O.Cl>C(OCC)C>[CH2:1]([O:8][C:9]1[C:14]2[CH:35]([C:34]([OH:37])=[O:32])[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 133645735-benzyloxy-4-cyano-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran

생성물 1

HCID 133645785-Benzyloxy-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran-4-carboxylic acid

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A mixture of 2.0 g 5-benzyloxy-4-cyano-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran, 20 g potassium hydroxide and 100 ml ethylene glycol are heated under nitrogen at reflux for 18 hours and cooled to ambient temperature. The mixture is acidified to pH 3 with concentrated hydrochloric acid, extracted with ethyl acetate and the extracts dried (MgSO4). Evaporation of solvent gives an oil which is taken up in ethyl ether, washed with water, brine, dried (MgSO4) and the solvent evaporated to give 2.09 g of crude solid. The crude was purified by chromatography on silica gel, eluting with ethyl ether/hexane. The combined product fractions are combined and solvent evaporated to afford 1.69 g of product, m.p. 137°-138° C.

후처리

  1. temperatureare heated under nitrogen
  2. temperatureat reflux for 18 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialthe extracts dried (MgSO4)
  5. customEvaporation of solvent
  6. customgives an oil which
  7. washwashed with water, brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated
  10. customto give 2.09 g of crude solid
  11. customThe crude was purified by chromatography on silica gel
  12. washeluting with ethyl ether/hexane
  13. customsolvent evaporated

출처 및 근거

ORD 기록
ord-7eef7580c1884634a145698deaed5405
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863934

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