Acetic Acid → HCID 67152942, compound

HRID 574055Notes

Reaction equation

HRID 574055 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][O:33]C3CCCCO3)[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:33][CH2:32][CH2:31][O:30][C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][OH:23])[CH:15]=1)([C:10]1[CH:9]=[CH:8][CH:7]=[CH:12][CH:11]=1)[C:40]1[CH:45]=[CH:44][C:53]([C:52]([OH:55])=[O:54])=[CH:42][CH:41]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 23692425Sodium hydroxide ethanolHCID 67152825HCID 67152825, compound

Product 1

HCID 67152942HCID 67152942, compound

Procedure

A solution of 4 (360 mg) in 3 mL of 80% aqueous acetic acid was heated at 75° C. for 12 h. 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 and 10 mL of ice cooled water was added to the residue and the aqueous solution was acidified with 1N HCl. The precipitated yellow solid was filtered and washed several times with water and dried under high vacuum. Yield: 270 mg (100%, 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. filtrationThe precipitated yellow solid was filtered
  7. washwashed several times with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-f39fe829cb9a4d1bbcce5e96ddf7036d
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Reaction notes

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