Acetic Anhydride → HCID 22759330, compound

HRID 460869Notes

Reaction equation

HRID 460869 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-d32c1d3e80b54578b00476f71cfcbe63
Source dataset
uspto-grants-1977_12
Patent number
US04061643

Reaction notes

Loading…