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1-Dodecanethiol → Dodecylsulfanyl-3-(2,4,6-trichloro-phenyl)-prop-2-en-1-ol

HRID 1039352
ノート
印刷プレビュー

反応式

HRID 1039352 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[C:10]#[C:11][CH2:12][OH:13].[OH-].[Na+].[CH2:16]([SH:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN1CCCC1=O.C(OCC)(=O)C.O>[CH2:16]([S:28][CH:12]([OH:13])[CH:11]=[CH:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[Cl:9])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 81951-DodecanethiolHCID 14798Sodium HydroxideHCID 702047693-(2,4,6-Trichloro-phenyl)-prop-2-yn-1-ol

生成物 1

HCID 67992103Dodecylsulfanyl-3-(2,4,6-trichloro-phenyl)-prop-2-en-1-ol収率 32.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate
溶媒
2 回
HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
22 °C

実験手順

To a solution of 3-(2,4,6-trichloro-phenyl)-prop-2-yn-1-ol (1.0 g; 4.2 mmol) in N-methyl-2-pyrrolidone (10 ml) and ethyl acetate (2 ml) at 2° C. was added sodium hydroxide (grind to powder) (0.19 g; 4.7 mmol). At 5° C. was added dropwise dodecanethiol (1.4 ml; 6.0 mmol). The reaction mixture was allowed to warm at 22° C. and was stirred for 30 min. The mixture was poured in water and ethyl acetate was added. Organic layer was washed three times with brine, dried over sodium sulfate and evaporated. The crude oil obtained was subject to flash chromatography (eluant: c-hexane/ethyl acetate 99:1 to 80:20) to afford 0.60 g (32% of theory) of dodecylsulfanyl-3-(2,4,6-trichloro-phenyl)-prop-2-en-1-ol as a yellow oil.

後処理

  1. washOrganic layer was washed three times with brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe crude oil obtained

出典と根拠

ORDレコード
ord-c06a6b2ba4e2431d9a1bcdc67adfc089
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08552049B2

反応ノート

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