Hydrochloric Acid → HCID 13611380, compound

HRID 359740Notes

Reaction equation

HRID 359740 reaction equation
[OH-].[Na+].[CH3:3][C:4]([C:7]1[CH:12]=[C:11]([SH:13])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:6])[CH3:5].Br[CH:20]1[CH2:25][CH2:24][O:23][C:21]1=[O:22].Cl>CO.O>[CH3:6][C:4]([C:7]1[CH:12]=[C:11]([S:13][CH:20]2[CH2:25][CH2:24][O:23][C:21]2=[O:22])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:3])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 13611380HCID 13611380, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (0.20 g, 5 mmole) was added to a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (1.11 g, 4.6 mmole) in methanol (20 ml) and stirred at room temperature until dissolved. 2-Bromobutyrolactone (0.82 g, 5 mmole) was added and the mixture was stirred at room temperature for 48 hours. The mixture was diluted with water, acidified with 1 N hydrochloric acid, and extracted with diethyl ether. The ether extract was washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in a minimum of hexane and cooled to induce crystallization. Chromatography of the solid on silica gel and recrystallization from hexane gave the title compound, m.p. 98°'100°.

Workup

  1. dissolutionuntil dissolved
  2. stirringthe mixture was stirred at room temperature for 48 hours
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in a minimum of hexane
  10. temperaturecooled
  11. customcrystallization
  12. customChromatography of the solid on silica gel and recrystallization from hexane

Sources & evidence

ORD record
ord-57ee59c4ba284bb6a08fee01244bf128
Source dataset
uspto-grants-1991_03
Patent number
US05002967

Reaction notes

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