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

HRID 2185120Notes

Reaction equation

HRID 2185120 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c234d6d1ad0948d48583ac04857da117
Source dataset
uspto-grants-2002_06
Patent number
US06399771B1

Reaction notes

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