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

HRID 359730

反応式

HRID 359730 の反応式
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].Br[CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22].[OH-].[K+].O>CC(C)=O>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:11][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:1])[CH3:3]

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

To a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.57 g, 15 mmole) and ethyl 4-bromobutyrate (3.23 g, 16.5 mmole) in 10 ml of acetone was added potassium hydroxide flakes (2.52 g, 45 mmole) Water (20 ml) was added and the solution was stirred for 1.5 hours, then concentrated in vacuo to dryness. Water (50 ml) was added to the residue and the aqueous mixture was washed with three portions (75 ml each) of ethyl acetate. The aqueous layer was separated and acidified with concentrated hydrochloric acid and extracted with two portions (50 ml each) of ethyl acetate. The organic layers were combined and washed with water, dried over sodium sulfate, filtered and concentrated in vacuo to an oil. Purification by chromatography on silica gel and recrystallization from diethyl ether-hexane yielded, after collection and drying in vacuo, the title compound, m.p. 112°-113.5°.

後処理

  1. additionwas added
  2. concentrationconcentrated in vacuo to dryness
  3. additionWater (50 ml) was added to the residue
  4. washthe aqueous mixture was washed with three portions (75 ml each) of ethyl acetate
  5. customThe aqueous layer was separated
  6. extractionextracted with two portions (50 ml each) of ethyl acetate
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo to an oil
  11. customPurification by chromatography
  12. customon silica gel and recrystallization from diethyl ether-hexane
  13. customyielded
  14. customafter collection
  15. customdrying in vacuo

出典と根拠

ORDレコード
ord-57fb6df0c5b64f429df904cecbeccedd
出典データセット
uspto-grants-1991_03
特許番号
US05002967

関連ノート

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