Acetic Acid → 12-(3,5-Di-tert-butyl-4-hydroxyphenylthio)dodecanoic acid

HRID 1090999ノート

反応式

HRID 1090999 の反応式
[C:1]([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])[CH3:2].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30].[OH-].[Na+].C(O)(=O)C>C(O)C.O>[C:1]([C:5]1[CH:10]=[C:9]([S:11][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 17546812-Bromododecanoic Acid

生成物 1

HCID 1479623112-(3,5-Di-tert-butyl-4-hydroxyphenylthio)dodecanoic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of 2,6-di-tert-butyl-4-mercaptophenol (II) (477 mg; 2 mmol) in dry ethanol (20 ml), water containing 12-bromododecanoic acid (558 mg; 2 mmol) and 97 % sodium hydroxide (250 mg; 6 mmol) was added, and the resultant mixture was allowed to stand at room temperature for 20 hours. The reaction mixture was made acidic with 10 aqueous acetic acid and extracted with ethyl acetate. The extract was washed two times with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product thus obtained was chromatographed on silica gel and eluted with ethyl acetate. The collected fractions were concentrated under reduced pressure. The residue was recrystallized from a mixture of water and methanol (1 : 1 by volume) to give the objective compound (Ie) (680 mg). Yield, 78 %. m.p., 41°-42° C.

後処理

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed two times with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1cad54b8c8e74ef6b54cbcb8bd641d67
出典データセット
uspto-grants-1992_01
特許番号
US05084214

反応ノート

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