Hydrochloric Acid → HCID 68861022, compound

HRID 384595Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:19](Cl)(=[O:23])[CH:20]([CH3:22])[CH3:21].ClC1C=CC=CC=1Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(OCC)(=O)C>[CH3:21][CH:20]([CH3:22])[C:19]([C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:4][C:3]([O:2][CH3:1])=[O:18])=[CH:7][CH:8]=1)=[O:23]

Participants

Conditions

Temperature: 4 °C

Procedure

A mixture of 80 g (0.333 mol) of methyl3,3-diphenylpropanoate, 42.6 g (0.399 mol) of isobutyryl chloride, and 600 mol of 1,2-dichlorobenzene is cooled to 4° C. Aluminum chloride (112 g, 0.832 mol) is added portion wise over 2 hours while the reaction temperature is kept between −5 and 5° C. The reaction is kept within this temperature range for 7 hours, and then stirred at room temperature for 13 hours. The reaction mixture is poured into a mixture of ice and concentrated hydrochloric acid, and then stirred for 1 hour. The organic layer is washed twice with dilute hydrochloric acid, and then concentrated under vacuum to give 115 grams of crude product. Purification by column chromatography on silica gel with 9:1 heptane:ethyl acetate as the eluent gives 69 g (60% yield) of methyl 3-[4-(2-methylpropionyl)phenyl]-3-phenylpropanoate.

Workup

customis kept between −5 and 5° C
stirringstirred for 1 hour
washThe organic layer is washed twice with dilute hydrochloric acid
concentrationconcentrated under vacuum
customto give 115 grams of crude product
customPurification by column chromatography on silica gel with 9:1 heptane

Sources & evidence

ORD record: ord-e1cd440c023a4dc18032e7d410431b06
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367743B2

Reaction notes

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