Hexane → HCID 10377834, compound

HRID 430718Notes

Reaction equation

HRID 430718 reaction equation
[Al+3].[Cl-:2].[Cl-:3].[Cl-].[C:5]1(=[O:12])[O:11][C:9](=[O:10])[CH2:8][C:6]1=[CH2:7].[CH3:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1C(Cl)=CC=C(Cl)C=1>[CH2:7]=[C:6]([CH2:8][C:9](=[O:10])[C:15]1[CH:14]=[CH:13][C:18]([Cl:2])=[C:17]([Cl:3])[CH:16]=1)[C:5]([OH:11])=[O:12]

Participants

5

Reactant 3

HCID 8058HexaneHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10377834HCID 10377834, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

Aluminium chloride anhydrous (53 g, 0.13 mol.) was added to a solution of itaconic anhydride (15 g, 0.13 mol.) in dichlorobenzene (100 mL) at room temperature. The reaction mixture was heated to 50° C. for 3 hours. and then inverse quenched with cold water/37% hydrochloric acid (100 mL/100 mL) maintaining the temperature below 30° C. After stirring the quenched reaction for 15 min., hexane (80 mL) was added and stirring continued for 0.5 hours. The product was filtered and dried in a vacuum oven to give the crude unsaturated-ketoacid as a colourless solid, 36 g, recrystallization from diethyl ether provided the pure acid (22 g, 67%) as colourless prisms melting at 156-57° C.

Workup

  1. customand then inverse quenched with cold water/37% hydrochloric acid (100 mL/100 mL)
  2. temperaturemaintaining the temperature below 30° C
  3. customthe quenched reaction for 15 min.
  4. stirringstirring
  5. filtrationThe product was filtered
  6. customdried in a vacuum oven
  7. customto give the crude unsaturated-
  8. customketoacid as a colourless solid, 36 g, recrystallization from diethyl ether

Sources & evidence

ORD record
ord-dcbb31ce2b30413ea053a445025cd1f9
Source dataset
uspto-grants-2001_11
Patent number
US06323240B1

Reaction notes

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