Benzene → 2-Pyrrolidinone, 5-phenyl-

HRID 2185119Notes

Reaction equation

HRID 2185119 reaction equation
C(O[CH:4]1[NH:9][C:7](=[O:8])[CH2:6][CH2:5]1)C.S(=O)(=O)(O)O.[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([CH:4]2[NH:9][C:7](=[O:8])[CH2:6][CH2:5]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 1118Sulfuric AcidHCID 35805555-Ethoxy-2-pyrrolidinone

Product 1

HCID 956722-Pyrrolidinone, 5-phenyl-Yield 100%

Procedure

At 0° C. 6.45 g of γ-ethoxy-γ-butyrolactam and 50 ml of concentrated sulphuric acid were charged initially, and 18.8 ml of benzene were added. After thawing, the mixture was stirred at room temperature for 4 days. For work-up, the mixture was poured onto ice, 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. 8.1 g (100% of theory) of γ-phenyl-γ-butyrolactam were obtained. 1H NMR (400 MHz, d6 DMSO) δ [ppm]: 1.75 (m, 1H); 2.23 (t, 2H); 2.45 (m, 1H); 4.67 (t, 1H); 7.26-7.39 (m, 5H); 8.08 (br, 1H).

Workup

  1. customAt 0° C
  2. additionFor work-up, the mixture was poured onto ice
  3. extractionextracted three times with ethyl acetate
  4. washthe combined extracts were washed once with water and once with saturated aqueous sodium chloride solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7b3c61ef2ffd43249e5baa2d08c234b2
Source dataset
uspto-grants-2002_06
Patent number
US06399771B1

Reaction notes

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