Sodium Hydroxide → HCID 13504778, compound

HRID 1719416Notes

Reaction equation

HRID 1719416 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 aqeuous solution was acidified to pH 3. 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-1da17b69b3354053a494f60caca239a8
Source dataset
uspto-grants-1985_09
Patent number
US04539419

Reaction notes

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