Water → Butanoic acid, 4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-

HRID 1085415

반응식

HRID 1085415 반응식
[OH-].[K+].[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].C([O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br)C.O>CC(C)=O>[CH3:6][C:4]([C:7]1[CH:12]=[C:11]([S:13][CH2:25][CH2:24][CH2:23][C:22]([OH:27])=[O:21])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18])([CH3:3])[CH3:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 76300Ethyl 4-bromobutyrate

생성물 1

HCID 9840255Butanoic acid, 4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Potassium hydroxide flakes (2.52 g, 0.045 mole) were added to a clear solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.57 g, 0.015 mole) and ethyl-4-bromobutyrate (3.23 g, 0.0165 mole) in acetone (10 ml). Water (20 ml) was added and the solution stirred for 1.5 hours, the solvent removed on a rotary evaporator and water (50 ml) added and extracted with ethyl ether (3×75 ml). The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl ether (2×50 ml), washed with water (50 ml), dried over sodium sulfate, filtered and the solvents removed, leaving an oil, which was purified by chromatography on silica, recrystallized from ethyl ether/Skellysolve B, filtered and the product dried in vacuo at room temperature for 12 hours, m.p. ca. 112°-113.5° C.

후처리

  1. customthe solvent removed on a rotary evaporator and water (50 ml)
  2. additionadded
  3. extractionextracted with ethyl ether (3×75 ml)
  4. extractionextracted with ethyl ether (2×50 ml)
  5. washwashed with water (50 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents removed
  9. customleaving an oil, which
  10. customwas purified by chromatography on silica
  11. customrecrystallized from ethyl ether/Skellysolve B
  12. filtrationfiltered
  13. customthe product dried in vacuo at room temperature for 12 hours

출처 및 근거

ORD 기록
ord-af704a3b2658452db63e823bf789ca61
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05010080

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