HCID 14330000, compound → HCID 14329999, compound

HRID 2164970Notes

Reaction equation

HRID 2164970 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-83d5be783a3b41e8aa83c3c09fab9137
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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