Acetic Anhydride → HCID 22759330, compound

HRID 329305Notes

Reaction equation

HRID 329305 reaction equation
[C:1]([CH:4]([CH2:14][CH2:15][CH2:16][CH:17]([OH:27])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29]>CCOCC>[C:1]([CH:4]([CH2:14][CH2:15][CH2:16][CH:17]([O:27][C:28](=[O:30])[CH3:29])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22759241HCID 22759241, compound

Product 1

HCID 22759330HCID 22759330, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8-acetyl-12-hydroxy-13-(4-fluorophenoxy)tridecanoic acid (9.5 g., 0.025 mole) and acetic anhydride (6.1 g., 0.06 mole) is heated at 60° for 18 hours. The mixture is then cooled and dissolved in 80 ml. of ether. The solution is extracted with an ice-cold solution of 8 g. of sodium hydroxide in 150 ml. of water. The basic solution is separated and acidified with concentrated hydrochloric acid. The oily acid that separates is taken up in ether, washed with water and dried over sodium sulfate. The ether is evaporated to leave the crude product as a viscous yellow oil.

Workup

  1. temperatureis heated at 60° for 18 hours
  2. temperatureThe mixture is then cooled
  3. dissolutiondissolved in 80 ml
  4. extractionThe solution is extracted with an ice-cold solution of 8 g
  5. customThe basic solution is separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customThe ether is evaporated

Sources & evidence

ORD record
ord-49b5f98cf5184bff8f90d9b6b876a3e8
Source dataset
uspto-grants-1977_04
Patent number
US04020177

Reaction notes

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