Acetic Acid → 5-(4-Hydroxyphenyl)pyrrolidin-2-one

HRID 650653노트

반응식

HRID 650653 반응식
C(O[CH:4]1[NH:9][C:7](=[O:8])[CH2:6][CH2:5]1)C.S(=O)(=O)(O)O.C(O)(=O)C.[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1CCCCC1.C(OCC)(=O)C>[OH:25][C:19]1[CH:24]=[CH:23][C:22]([CH:4]2[NH:9][C:7](=[O:8])[CH2:6][CH2:5]2)=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 996PhenolHCID 1118Sulfuric AcidHCID 35805555-Ethoxy-2-pyrrolidinone

생성물 1

HCID 111165955-(4-Hydroxyphenyl)pyrrolidin-2-one수율 26.3%

시약·촉매·용매 1

HCID 21867204Cyclohexane ethylacetate용매

실험 절차

12.9 g of γ-ethoxy-γ-butyrolactam, 10 ml of concentrated sulphuric acid and 90 ml of glacial acetic acid were charged initially at 0° C. and admixed a little at a time with a total of 18.8 g of phenol. After thawing, the mixture was stirred at room temperature for 2 days. For work-Up, the mixture was poured onto ice and extracted three times with ethyl acetate, and the combined extracts were washed once with water and once with saturated aqueous sodium chloride solution, dried and evaporated. After some time, γ-2-hydroxyphenyl-γ-butyrolactam (XI-2b) of melting point 220° C. (6.4 g, 36% of theory) crystallized from the aqueous phase. The residue obtained on evaporation was stirred with 1:1 mixture of cyclohexane/ethyl acetate and afforded on filtration with suction 4.65 g of γ-4-hydroxyphenyl-γ-butyrolactam (XI-2a) of melting point 183° C. The filtrate was evaporated. Recrystallization from dichloromethane/hexane gave a further 3.35 g (total 45% of theory) of γ-4-hydroxyphenyl-γ-butyrolactam.

후처리

  1. additionFor work-Up, the mixture was poured onto ice
  2. extractionextracted three times with ethyl acetate
  3. washthe combined extracts were washed once with water and once with saturated aqueous sodium chloride solution
  4. customdried
  5. customevaporated
  6. customAfter some time, γ-2-hydroxyphenyl-γ-butyrolactam (XI-2b) of melting point 220° C. (6.4 g, 36% of theory) crystallized from the aqueous phase
  7. customThe residue obtained on evaporation

출처 및 근거

ORD 기록
ord-53e7c998405a4ec096fdb5906b977933
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274613B1

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