Coumarin → HCID 23054125, compound

HRID 1172031Notes

Reaction equation

HRID 1172031 reaction equation
C(OC(=O)C)(=O)C.[O:8]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:9]1=[O:10].C(O)(=O)C.C(O)(=O)C.[I:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.S(=O)(=O)(O)O.[F:39][P-:40]([F:45])([F:44])([F:43])([F:42])[F:41].[K+]>ClCCl>[F:39][P-:40]([F:45])([F:44])([F:43])([F:42])[F:41].[C:28]1([I+:27][C:16]2[CH:17]=[C:18]3[C:13]([CH:12]=[CH:11][C:9](=[O:10])[O:8]3)=[CH:14][CH:15]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 323CoumarinHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 12217721Iodo benzene diacetateHCID 23688904Potassium hexafluorophosphate

Product 1

HCID 23054125HCID 23054125, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 80 ml of acetic anhydride was suspended 7.3 g (0.05 mol) of coumarin and 16.1 g (0.05 mol) of iodobenzene diacetate, and 10 g (0.1 mol) of concentrated sulfuric acid was added dropwise thereto at 0 to 7° C. for 1 hour, followed by gradually warming to room temperature and reacting with stirring for 8 hours. After completion of the reaction, the reaction solution was poured in 200 ml of ice water, and 150 ml of dichloromethane was added thereto to dissolve insoluble substance. Then 18.4 g (0.1 mol) of potassium hexafluorophosphate was added to the obtained solution, followed by stirring at room temperature for 2 hours. The dichloromethane layer obtained by fractionation was washed with 100 ml of water twice. The obtained dichloromethane layer was semi concentrated under reduced pressure and the precipitated crystal was filtered off, followed by drying under vacuum at 50° C. for 2 hours to obtain 2.4 g of objective substance as pale yellow crystal (yield: 10%).

Workup

  1. additionwas added dropwise
  2. customAfter completion of the reaction
  3. dissolutionto dissolve insoluble substance
  4. stirringby stirring at room temperature for 2 hours
  5. washwas washed with 100 ml of water twice
  6. concentrationThe obtained dichloromethane layer was semi concentrated under reduced pressure
  7. filtrationthe precipitated crystal was filtered off
  8. customby drying under vacuum at 50° C. for 2 hours

Sources & evidence

ORD record
ord-2715625f38fc427f96550f7afa48274c
Source dataset
uspto-grants-2010_11
Patent number
US07833691B2

Reaction notes

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