Sulfuric Acid → 5-Hydroxy-1-methyl-5-(3-methylphenyl)pyrrolidin-2-one

HRID 268286Notes

Reaction equation

HRID 268286 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH3:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].S(=O)(=O)(O)O>C1C=CC=CC=1.C(OCC)C>[OH:16][C:15]1([C:2]2[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=2)[N:11]([CH3:10])[C:12](=[O:17])[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 115603-BromotolueneHCID 707172,5-Pyrrolidinedione, 1-methyl-HCID 5462224Magnesium

Product 1

HCID 30423595-Hydroxy-1-methyl-5-(3-methylphenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a Grignard prepared from 27.3g (0.16 mole) of 3-bromotoluene and 3.7 g. (0.16 mole) of magnesium turnings in 100 ml. of dry diethylether, there is added dropwise over a period of about 10 minutes 12.2 g. (0.11 mole) of N-methylsuccinimide in 100 ml. of dry benzene. The resulting mixture is stirred and refluxed for about 4 hours and then allowed to stand overnight at room temperature. Stirring is resumed and 40 ml. of 50% sulfuric acid is added dropwise at such a rate to maintain a gentle reflux. After an additional 0.5 hours, the water layer is separated and washed twice with 50 ml. of benzene. The organic layers are combined and washed with 50 ml. of sodium carbonate and then twice more with 50 ml. of water. The resulting layer is dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The resulting residue is crystallized from methylene chloride/hexane to give 5-hydroxy-1-methyl-5-(m-tolyl) pyrrolidone; m.p. 128°-130°C.

Workup

  1. temperaturerefluxed for about 4 hours
  2. stirringStirring
  3. temperatureto maintain a gentle reflux
  4. waitAfter an additional 0.5 hours
  5. customthe water layer is separated
  6. washwashed twice with 50 ml
  7. washwashed with 50 ml
  8. dry with materialThe resulting layer is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe resulting residue is crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-b2d07190ad0845dd98bbc3e2d03676ca
Source dataset
uspto-grants-1976_03
Patent number
US03947460

Reaction notes

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