Sodium Hydroxide → HCID 13504778, compound

HRID 1981992Notes

Reaction equation

HRID 1981992 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:39](=[O:41])[CH3:40])[C:10]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[C:28]([OH:35])[C:27]=3[CH2:36][CH2:37][CH3:38])=[CH:11][CH:12]=2)[CH:7]=1.[OH-].[Na+]>CO>[C:39]([C:9]1[C:10]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[C:28]([OH:35])[C:27]=2[CH2:36][CH2:37][CH3:38])=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[C:6]([O:5][CH2:4][C:3]([OH:42])=[O:2])[CH:15]=[CH:14]2)(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54563510HCID 54563510, compound

Product 1

HCID 13504778HCID 13504778, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.8 g of [[8-acetyl-7-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester and 31 ml of 1N sodium hydroxide in 60 ml of methanol was stirred at reflux for 1 hour. The methanol was removed in vacuo and the aqueous solution was acidified to pH3. The gummy precipitate was extracted with methylene chloride, washed with water, dried (magnesium sulfate) and concentrated in vacuo to give an oil which was triturated with ether to yield 1.56 g, m.p. 110°-111° C. (89%) of [[8-acetyl-7-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe methanol was removed in vacuo
  3. extractionThe gummy precipitate was extracted with methylene chloride
  4. washwashed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-612b264c611345bd8cb926aae4f23038
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

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