Acetic Acid → HCID 52933493, compound

HRID 574056Notes

Reaction equation

HRID 574056 reaction equation
CC1(C)COC([C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:40]3[CH:45]=[CH:44]C=[CH:42][CH:41]=3)([O:30][CH2:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][O:23]C4CCCCO4)[CH:15]=3)=[CH:9][CH:8]=2)=N1.[OH-].[Na+].CCO.[C:52]([OH:55])(=[O:54])[CH3:53]>>[OH:23][CH2:22][CH2:21][O:20][C:16]1[CH:15]=[C:14]([C:13]([C:10]2[CH:9]=[CH:8][CH:7]=[CH:12][CH:11]=2)([O:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[CH:41]=[CH:42][C:53]([C:52]([OH:55])=[O:54])=[CH:44][CH:45]=2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 23692425Sodium hydroxide ethanolHCID 67152990HCID 67152990, compound

Product 1

HCID 52933493HCID 52933493, compound

Procedure

A solution of 7 (550 mg) in 3 mL of 80% aqueous acetic acid was heated at 75° C. for overnight. Then the solution was evaporated and the residue obtained was refluxed with 20% NaOH/EtOH (1:1, v/v, 3 mL) for 2 h. The solvent was removed, 10 mL of ice cooled water was added to the residue and the aqueous solution acidified with 1N HCl, extracted with CH2Cl2 (60 mL) and dried over anhydrous Na2SO4. Evaporation of the solvent gave yellow solid Yield: 485 mg (quantitative).

Workup

  1. customThen the solution was evaporated
  2. customthe residue obtained
  3. customThe solvent was removed
  4. temperature10 mL of ice cooled water
  5. additionwas added to the residue
  6. extractionextracted with CH2Cl2 (60 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a7fa11d55c594bbeba207b7be1cd0ceb
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Reaction notes

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