Benzene → HCID 11830208, compound

HRID 2221101Notes

Reaction equation

HRID 2221101 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][C:8]1=[CH2:9].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[CH2:9]=[C:8]([CH2:10][C:11](=[O:12])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:7]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11830208HCID 11830208, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred slurry of benzene (4.50 mL, 50.3 mmol) and itaconic anhydride (5.64 g, 50.3 mmol) in 1,2-dichloroethane at room temperature under argon, was added aluminum chloride (13.42 g, 100.7 mmol) in portions over 30 min A dark green solution formed as the temperature rose to 27° C. before subsiding. After 4 h, the now brown solution was poured rapidly into a stirred mixture of ice (200 g) and concentrated hydrochloric acid (15 mL). The resulting beige solids were filtered and air-dried to give the title compound (4.69 gm, 49%). MS [M+H]+: found 191.

Workup

  1. customformed as the temperature
  2. customrose to 27° C. before subsiding
  3. filtrationThe resulting beige solids were filtered
  4. customair-dried

Sources & evidence

ORD record
ord-c92d7ac77f2d4a1d83f62df712f51d92
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Reaction notes

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