Hydrochloric Acid → HCID 131716693, compound

HRID 1073470Notes

Reaction equation

[CH3:1][CH:2]([CH2:6][CH3:7])[C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[C:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:24][CH:25]([CH2:29][CH3:30])[C:26]([O-:28])=[O:27].Cl>[N+](C1C=CC=CC=1)([O-])=O>[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([C:21]1[CH:22]=[CH:23][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:19][CH:20]=1)=[O:4].[CH3:24][CH:25]([CH2:29][CH3:30])[C:26]([O-:28])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

Then, 4.0 g of (+)-2-methyl butanoyl chloride and 7 ml of nitrobenzene were charged into a flask and cooled to 0° C., added with 10.74 g (80 mmol) of anhydrous aluminum chloride and further with a solution of 4.97 g (19.6 mmol) of (+)-biphenyl-2-methylbutanoate in 9 ml of nitrobenzene, which was stirred at room temperature for 70 hours. After the addition of 2 normal hydrochloric acid and ice, the extraction with chloroform was performed. The extracted chloroform phase was washed with water, dried on anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified through a column chromatography of silica gel after distillation off of the solvent to obtain 3.60 g (yield: 54%) of an oily (+)-4-(2-methylbutanoyl) biphenyl-2-methylbutanoate. The NMR analytical values of this product were as follows.

Workup

extractionthe extraction with chloroform
washThe extracted chloroform phase was washed with water
dry with materialdried on anhydrous magnesium sulfate
distillationthe solvent was distilled off
customThe residue was purified through a column chromatography of silica gel
distillationafter distillation off of the solvent

Sources & evidence

ORD record: ord-637f9b35957248cc84ddb4d48433ba59
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04970023

Reaction notes

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