Hydrochloric Acid → HCID 54273732, compound

HRID 1763080Notes

Reaction equation

HRID 1763080 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:16][CH:17]=[C:18]([Cl:20])[CH3:19])([CH2:13][CH2:14][CH3:15])[C:8]2=[O:12])=[CH:4][C:3]=1[CH:21]([CH2:25][C:26]([OH:28])=[O:27])C(O)=O.Cl>[Cu].N1C2C(=CC=CC=2)C=CC=1>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:16][CH:17]=[C:18]([Cl:20])[CH3:19])([CH2:13][CH2:14][CH3:15])[C:8]2=[O:12])=[CH:4][C:3]=1[CH2:21][CH2:25][C:26]([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54141677HCID 54141677, compound

Product 1

HCID 54273732HCID 54273732, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

[6,7-Dichloro-2-(3-chloro-2-butenyl)-2,3-dihydro-1-oxo-2-propyl-1H-inden-5-yl]succinic acid (7.9 g, 0.01764 mole) was combined with quinoline (70 ml) and copper powder (2.9 g), stirred under N2 at 130°-135° C. (internal) in an oil bath for 1/2 hour. The mixture was poured into ice water, acidified with hydrochloric acid and extracted with methylene chloride. The organic extracts were washed with dilute HCl, H2O, dried over MgSO4 and concentrated under vacuum. The residue was chromatographed on silica eluting with methylene chloride, tetrahydrofuran, acetic acid (100:1:1) to obtain 7 g of the product as an oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed with dilute HCl, H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was chromatographed on silica eluting with methylene chloride, tetrahydrofuran, acetic acid (100:1:1)

Sources & evidence

ORD record
ord-f3e293d85fa549d397af52acabc650dc
Source dataset
uspto-grants-1989_05
Patent number
US04835313

Reaction notes

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