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

HRID 1039352
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인쇄 미리보기

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HRID 1039352 반응식
[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]
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate
용매
2회
HCID 13387N-methyl-2-pyrrolidone용매

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온도
22 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c06a6b2ba4e2431d9a1bcdc67adfc089
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552049B2

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