Hydrochloric Acid → HCID 13826426, compound

HRID 1906923Notes

Reaction equation

HRID 1906923 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1.C([C:14]1([CH:22]([CH3:26])C([O-])=O)[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]1[CH3:21])C.Cl>C(Cl)Cl>[Cl:20][C:17]1[CH:16]=[C:15]([CH3:21])[C:14]([CH2:22][CH2:26][C:8]([O:10][CH2:5][CH3:6])=[O:9])=[CH:19][C:18]=1[C:8](=[O:9])[CH2:7][CH2:6][C:5]([OH:10])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 86741394HCID 86741394, compound

Product 1

HCID 13826426HCID 13826426, compoundYield 166.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (5.87 g; 0.044 mole) was added portionwise (5 minutes) to a mixture of succinic anhydride (1.1 g; 0.011 mole) and 1-ethyl-4-chloro-2-methylphenylpropionate (2.27 g; 0.01 mole) in CH2Cl2 (20 ml) with cooling (ice bath). The reaction mixture was stirred at room temperature for 24 hours, poured into ice and 10 ml concentrated HCl and extracted with ether. The ether solution was dried and evaporated to give a yellow brown oil, which was purified by flash column chromatography (silica gel and 2% HOAc-10% acetone-90% CH2Cl2) to give the product as a yellow oil (3.0 g; 92% yield).

Workup

  1. temperaturewith cooling (ice bath)
  2. extractionextracted with ether
  3. dry with materialThe ether solution was dried
  4. customevaporated
  5. customto give a yellow brown oil, which
  6. customwas purified by flash column chromatography (silica gel and 2% HOAc-10% acetone-90% CH2Cl2)

Sources & evidence

ORD record
ord-640050f3aa9f4d9a812e2b387412deb4
Source dataset
uspto-grants-1987_03
Patent number
US04654363

Reaction notes

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