Hydrochloric Acid → [4-(4-Chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester

HRID 1581853Notes

Reaction equation

HRID 1581853 reaction equation
[ClH:1].[CH:2]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3]1>C(O)C.C1(C)C=CC=CC=1>[Cl:1][CH2:4][CH2:3][CH2:2][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67524057[4-(Cyclopropylcarbonyl)pheny]methyl-propanedioic acid, dimethyl ester

Product 1

HCID 86585530[4-(4-Chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
68 °C

Procedure

Bubble hydrogen chloride gas through a solution of [4-(cyclopropylcarbonyl)phenyl]methyl-propanedioic acid, dimethyl ester (315 mg, 1.1 mmol) in ethanol (3 mL) and toluene (9 mL) for 10 minutes. Heat the solution to 68° C. After 4 hours, cool the solution to room temperature and bubble nitrogen through the solution for 1 hour. Add ethyl acetate and water to the residue. Dry the organic phase over anhydrous magnesium sulfate and concentrate to give the title compound (321 mg, 91%).

Workup

  1. temperaturecool the solution to room temperature
  2. custombubble nitrogen through the solution for 1 hour
  3. dry with materialDry the organic phase over anhydrous magnesium sulfate
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-6defcd7170f04d81aa0dc92fb3fc91e5
Source dataset
uspto-grants-2004_05
Patent number
US06730791B2

Reaction notes

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