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

HRID 650653ノート

反応式

HRID 650653 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 111165955-(4-Hydroxyphenyl)pyrrolidin-2-one収率 26.3%

試薬・触媒・溶媒 1

HCID 21867204Cyclohexane ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-53e7c998405a4ec096fdb5906b977933
出典データセット
uspto-grants-2001_08
特許番号
US06274613B1

反応ノート

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