Hydrochloric Acid → (+)-4-(2-Methyloctanoyl) biphenyl 2-methyloctanoate

HRID 1073474Notes

Reaction equation

HRID 1073474 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.C1(C2C=CC=CC=2)C=CC=CC=1.[CH3:40][CH:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:42]([OH:44])=[O:43].Cl>[N+](C1C=CC=CC=1)([O-])=O>[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].[CH3:40][CH:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:42]([O-:44])=[O:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 128122322-Methyl octanoic acid chlorideHCID 131716695(+)-Biphenyl 2-methyloctanoate biphenyl

Product 1

HCID 131716694(+)-4-(2-Methyloctanoyl) biphenyl 2-methyloctanoateYield 49%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

Next, 2.02 g (11.4 mmol) of the above (+)-2-methyl octanoyl chloride and 3 ml of nitrobenzene were cooled to 0° C. in a flask and added with 3.06 g (22.9 mmol) of anhydrous aluminum chloride with stirring, which were stirred at room temperature for 30 minutes. Thereafter, 2.89 g (7 mmol) of (+)-biphenyl-2-methyloctanoate biphenyl dissolved in 3 ml of nitrobenzene was added thereto, which was reacted by stirring at room temperature for 140 hours. After the completion of the reaction, 2 normal hydrochloric acid and ice were added and extracted with chloroform. The extract was washed with water, dried on anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified through a column chromatography of silica gel to obtain 1.55 g (yield: 49%) of an oily (+)-4-(2-methyloctanoyl) biphenyl-2-methyloctanoate.

Workup

  1. stirringwhich were stirred at room temperature for 30 minutes
  2. additionwas added
  3. customwhich was reacted
  4. stirringby stirring at room temperature for 140 hours
  5. additionwere added
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. dry with materialdried on anhydrous magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent
  11. customThe residue was purified through a column chromatography of silica gel

Sources & evidence

ORD record
ord-ab71cc87a6e14ab1b29f7fed5de0cda3
Source dataset
uspto-grants-1990_11
Patent number
US04970023

Reaction notes

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