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

HRID 1039352Notes

Reaction equation

HRID 1039352 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
22 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c06a6b2ba4e2431d9a1bcdc67adfc089
Source dataset
uspto-grants-2013_10
Patent number
US08552049B2

Reaction notes

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