Hydrochloric Acid → (+)-2-Methyloctanoic acid 4-(2-methyloctanoyl) biphenyl

HRID 846559Notes

Reaction equation

HRID 846559 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[C:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:28][CH:29]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:30]([OH:32])=[O:31].Cl>[N+](C1C=CC=CC=1)([O-])=O>[CH3:28][CH:29]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:30]([OH:32])=[O:31].[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([C:25]1[CH:26]=[CH:27][C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:23][CH:24]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 128122322-Methyl octanoic acid chlorideHCID 67826054(+)-2-Methyloctanoic acid biphenyl

Product 1

HCID 67913760(+)-2-Methyloctanoic acid 4-(2-methyloctanoyl) biphenylYield 49%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

Next, 2.02 g (11.4 mmol) of the above (+)-2-methyloctanoic acid chloride and 3 ml of nitrobenzene were charged into a flask, and cooled to 0° C., to which was added 3.06 g (22.9 mmol) of anhydrous aluminum chloride with stirring and then the resulting mixture was stirred at room temperature for 30 minutes. This mixture was added with a solution of 2.89 g (7 mmol) of (+)-2-methyloctanoic acid biphenyl dissolved in 3 ml of nitrobenzene, which was reacted at room temperature for 140 hours with stirring. After the completion of the reaction, 2N hydrochloric acid and ice were added, and the extraction with chloroform was carried out, and the extract was washed with water, dried on anhydrous magnesium sulfate, distilled to remove the solvent, and purified by a column chromatography of silica gel to obtain 1.55 g (yield 49%) of an oily (+)-2-methyloctanoic acid-4-(2-methyloctanoyl) biphenyl.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. customwhich was reacted at room temperature for 140 hours
  3. stirringwith stirring
  4. additionwere added
  5. extractionthe extraction with chloroform
  6. washthe extract was washed with water
  7. dry with materialdried on anhydrous magnesium sulfate
  8. distillationdistilled
  9. customto remove the solvent
  10. custompurified by a column chromatography of silica gel

Sources & evidence

ORD record
ord-e4d8a46715dd4bb5804583d7414ffe70
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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