Sodium Hydroxide → 7-(4-Octylphenyl)hept-5-ynoic acid

HRID 1995777Notes

Reaction equation

HRID 1995777 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:24].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[OH-].[Na+]>CN(C)C=O>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][C:21]([OH:24])=[O:22])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2724130Cornforth reagentHCID 204880187-(4-Octylphenyl)hept-5-yn-1-ol

Product 1

HCID 204880227-(4-Octylphenyl)hept-5-ynoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-[p-(n-octyl)phenyl]-5-heptyn-1-ol (1.7 mmole) is dissolved in dimethyl formamide and to the resulting solution is added, with stirring, pyridinium dichromate (11.7 mmoles). After stirring for 48 hours at room temperature, the reaction mixture is poured onto a 10% sodium hydroxide solution and extracted with ethyl ether. The aqueous layer is acidified to pH of 2-3 with concentrated hydrochloric acid and extracted with chloroform. The chloroform layer is separated, the solvents removed by evaporation and the residue distilled under reduced pressure to afford the title compound, 7-[p-(n-octyl)phenyl]hept-5-ynoic acid.

Workup

  1. additionis added
  2. stirringAfter stirring for 48 hours at room temperature
  3. extractionextracted with ethyl ether
  4. extractionextracted with chloroform
  5. customThe chloroform layer is separated
  6. customthe solvents removed by evaporation
  7. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-4f00bb80e22344f490a67ee6ea358a33
Source dataset
uspto-grants-1983_09
Patent number
US04405810

Reaction notes

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