Acetic Anhydride → HCID 14579756, compound

HRID 1607293Notes

Reaction equation

HRID 1607293 reaction equation
[C:1]1([CH:7]([O:11][C:12]2[C:17]([Cl:18])=[CH:16][C:15]([CH2:19][CH2:20][CH3:21])=[C:14](O)[C:13]=2[C:23](=O)[CH3:24])C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([O-:29])(=[O:28])[CH3:27].[Na+].C(OC(=O)C)(=O)C>C(OCC)C>[C:26]([O:29][C:14]1[C:13]2[C:23]([CH3:24])=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:11][C:12]=2[C:17]([Cl:18])=[CH:16][C:15]=1[CH2:19][CH2:20][CH3:21])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 14579755HCID 14579755, compound

Product 1

HCID 14579756HCID 14579756, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-phenyl-2-(2-acetyl-3-hydroxy-4-propyl-6-chlorophenoxy) acetic acid (Step b)(3.4 g, 9.3 mmol), anhydrous sodium acetate (6.8 g, 82 mmol) and acetic anhydride (50 mL) was refluxed for 1 hour. The mixture was cooled, diluted with diethyl ether and the salts filtered off. The filtrate was concentrated and the residue chromatographed on silica gel with 10% ethyl acetate in hexane to obtain the title compound, m.p. 86°-87° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThe mixture was cooled
  3. filtrationthe salts filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue chromatographed on silica gel with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e4d73c17d5194d03ab59700d39e33cf7
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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