HCID 14098152, compound → HCID 14099847, compound

HRID 569298Notes

Reaction equation

HRID 569298 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:15])[C:10](=[CH2:14])[CH2:11][CH2:12][Cl:13])[CH:5]=[CH:4][C:3]=1[O:16][CH3:17]>C(Cl)Cl>[Cl:13][CH2:12][CH2:11][CH:10]1[CH2:14][C:5]2[C:6](=[C:7]([Cl:8])[C:2]([Cl:1])=[C:3]([O:16][CH3:17])[CH:4]=2)[C:9]1=[O:15]

Participants

3

Reactant 1

HCID 14098152HCID 14098152, compound

Product 1

HCID 14099847HCID 14099847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dichloro-4-(4-chloro-2-methylenebutyryl)anisole (14 gm, 0.037 mole) was dissolved in methylene chloride (7 ml) and added with stirring concentrated to sulfuric acid (55 ml) over a period of 20 minutes. The temperature rose to 39° C. The mixture was stirred for 16 hours at ambient temperature, then poured into ice water, extracted first with methylene chloride and then with ether. The combined organic extracts were washed with water, dried over MgSO4 and evaporated in vacuo. The residue (12 gm) was triturated with isopropyl alcohol, filtered and dried to give the product, m.p. 103°-105° C.

Workup

  1. additionadded
  2. concentrationconcentrated to sulfuric acid (55 ml) over a period of 20 minutes
  3. customrose to 39° C
  4. stirringThe mixture was stirred for 16 hours at ambient temperature
  5. additionpoured into ice water
  6. extractionextracted first with methylene chloride
  7. washThe combined organic extracts were washed with water
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue (12 gm) was triturated with isopropyl alcohol
  11. filtrationfiltered
  12. customdried
  13. customto give the product, m.p. 103°-105° C.

Sources & evidence

ORD record
ord-25ebcb6147d349aa928fe96f9c410ac4
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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