Hydrochloric Acid → HCID 53875126, compound

HRID 369922Notes

Reaction equation

HRID 369922 reaction equation
[CH3:1][N:2]1[CH:6]([CH3:7])[CH2:5][C:4]([C:14]2[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=[O:21].Cl.C[OH:24]>ClCCl>[CH3:1][N:2]1[CH:6]([CH3:7])[CH2:5][C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[OH:24])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:3]1=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 23282329HCID 23282329, compound

Product 1

HCID 53875126HCID 53875126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-60 °C

Procedure

(+/-)-1,5-dimethyl-3-(p-hydroxyphenyl)-3-phenyl-2-pyrrolidone (from Example 1), 1.5 g, was dissolved in 30 mL dichloromethane. The flask was flushed with argon and chilled in an acetone/dry ice bath to -60° C. I M boron tribromide in dichloromethane, 10 mL, was then added drop-wise over 18 min with stirring. The reaction was allowed to come to room temperature and stirred for 22 h. Methanol, 10 mL, was then added slowly to quench the reaction. The resultant solution was rotary evaporated to give an oil redissolved in 10 mL methanol and rotary evaporated a second time. The oil was diluted with 20 mL water to give a precipitate. 6 N hydrochloric acid, 6 mL, was added followed by 50 mL dichloromethane. Mixing gave a biphasic solution. The phases were separated and the upper aqueous phase was reextracted twice with 25 mL portions of dichloromethane. The combined dichloromethane extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, and evaporated to give a foam residue.

Workup

  1. customThe flask was flushed with argon
  2. additionI M boron tribromide in dichloromethane, 10 mL, was then added drop-wise over 18 min
  3. customto come to room temperature
  4. stirringstirred for 22 h
  5. additionMethanol, 10 mL, was then added slowly
  6. customto quench
  7. customthe reaction
  8. customThe resultant solution was rotary evaporated
  9. customto give an oil
  10. customrotary evaporated a second time
  11. additionThe oil was diluted with 20 mL water
  12. customto give a precipitate
  13. additionMixing
  14. customgave a biphasic solution
  15. customThe phases were separated
  16. washThe combined dichloromethane extracts were washed with saturated sodium chloride solution
  17. dry with materialdried over sodium sulfate
  18. customevaporated
  19. customto give a foam residue

Sources & evidence

ORD record
ord-08ff95d7f4de45678caefaeccc2e5940
Source dataset
uspto-grants-2000_10
Patent number
US06140137

Reaction notes

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