Acetic Acid → HCID 71548220, compound

HRID 512929Notes

Reaction equation

HRID 512929 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]([O:23][CH2:24][CH3:25])[CH2:21][OH:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.Cl([O-])=[O:27].[Na+].[Br-].[K+].C(O)(=O)C>ClCCl.CC1(C)N([O])C(C)(C)CCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]([O:23][CH2:24][CH3:25])[C:21]([OH:27])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 253877Potassium BromideHCID 23668197Sodium ChloriteHCID 71548221HCID 71548221, compound

Product 1

HCID 71548220HCID 71548220, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethoxy-alcohol 52 (30 g, 0.085 mol) in dichloromethane (300 ml) was added catalytic TEMPO (0.265 g, 0.0017 mol) and stirred for 10 minutes. To the above solution 100 ml aqueous solution containing mixture of sodium chlorite (23 g, 0.25 mol) and potassium bromide (5 g, 0.0425 mol) was added and stirred for 5 minutes. To this reaction mixture was added aq. acetic acid (5 ml, 20%) and stirring was continued for 12 hour at ambient temperature. The reaction mixture was filtered and the solid was washed with D.M. Water (500 ml) followed by washing with dichloromethane (200 ml). Toluene (400 ml) was added to the solid obtained and the resulting mixture was concentrated azeotropically till the volume of mixture remains to 150 ml and cooled in ice bath. The resulting suspension was filtered. The solid obtained was washed with hexane and dried in vacuum to yield ethoxy-acid 53 (25 g, 80.6%).

Workup

  1. additionwas added
  2. stirringstirred for 5 minutes
  3. stirringstirring
  4. waitwas continued for 12 hour at ambient temperature
  5. filtrationThe reaction mixture was filtered
  6. washthe solid was washed with D.M
  7. washby washing with dichloromethane (200 ml)
  8. additionToluene (400 ml) was added to the solid
  9. customobtained
  10. concentrationthe resulting mixture was concentrated azeotropically till the volume of mixture
  11. temperaturecooled in ice bath
  12. filtrationThe resulting suspension was filtered
  13. customThe solid obtained
  14. washwas washed with hexane
  15. customdried in vacuum

Sources & evidence

ORD record
ord-953b542e12124cac910c44cc115b99d3
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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