HCID 21319307, compound → HCID 21319303, compound

HRID 262590Notes

Reaction equation

HRID 262590 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:34]=[CH:33][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[H][H]>C(O)(=O)C.O=[Pt]=O>[CH2:1]([O:3][C:4]([C:6]1[CH:34]=[CH:33][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 21319307HCID 21319307, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21319303HCID 21319303, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

1-(4-ethoxycarbonylphenoxy)-14-(4-chlorophenoxy)-tetradec 9-yne (2.00 g.; 0.0041 M.) in acetic acid (15 ml.) was reduced in the presence of hydrogen and PtO2 (0.05 g.) at 60° C. and atmospheric pressure. When hydrogen absorption was complete the solution was filtered, the catalyst washed well with ethanol and the solvents evaporated under reduced pressure to yield a colourless oil. 1-(4-ethoxycarbonylphenoxy)-14-(4-chlorophenoxy)-tetradecane (1.62 g.; 80%) M.P. 72.5°-73.5° C. was obtained as a pure crystalline compound by chromatography of this oil on silica-gel (100 g.).

Workup

  1. customWhen hydrogen absorption
  2. filtrationwas filtered
  3. washthe catalyst washed well with ethanol
  4. customthe solvents evaporated under reduced pressure
  5. customto yield a colourless oil

Sources & evidence

ORD record
ord-39b2cc1b50154b299fa36eda4c368a5a
Source dataset
uspto-grants-1979_05
Patent number
US04154850

Reaction notes

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