HCID 14330000, compound → HCID 14329999, compound

HRID 2231494Notes

Reaction equation

HRID 2231494 reaction equation
C([O:3][C:4](=[O:44])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[C:32]([Cl:33])=[CH:31][C:30]([C:34](=[O:36])[CH3:35])=[C:29]([OH:37])[C:28]=2[CH2:38][CH2:39][CH3:40])[C:10]=1[CH2:41][CH2:42][CH3:43])C>[OH-].[Na+].CO>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:44])=[O:3])=[C:10]([CH2:41][CH2:42][CH3:43])[C:11]=1[O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[C:32]([Cl:33])=[CH:31][C:30]([C:34](=[O:36])[CH3:35])=[C:29]([OH:37])[C:28]=1[CH2:38][CH2:39][CH3:40])(=[O:17])[CH3:16]

Participants

4

Reactant 1

HCID 14330000HCID 14330000, compound

Product 1

HCID 14329999HCID 14329999, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.506 g of 4-[4-acetyl-3-[3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-propylphenoxy]butanoic acid ethyl ester in 4.0 ml of 1.0N sodium hydroxide and 20 ml of methanol was stirred at reflux for 2 hours. The methanol was removed in vacuo and the residue was acidified. The product was extracted with ethyl acetate and the dried (magnesium sulfate) extract was concentrated in vacuo to give 0.461 g (95% yield) of 4-[4-acetyl-3-[3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-propylphenoxy]butanoic acid as an oil.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe methanol was removed in vacuo
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialthe dried (magnesium sulfate)
  5. extractionextract
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-8e630988e3c34384bca3d4001f949620
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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