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

HRID 978008

反応式

HRID 978008 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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. The organic layer was 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.

後処理

  1. customthe solvent removed on a rotary evaporator and water (50 ml)
  2. additionadded
  3. extractionThe organic layer was extracted 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

出典と根拠

ORDレコード
ord-06f3860d79414ed4bf734780194a4409
出典データセット
uspto-grants-1987_05
特許番号
US04663333

関連ノート

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