Sodium Hydroxide → 4-[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]butanoic acid

HRID 1719423Notes

Reaction equation

HRID 1719423 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:38](=[O:40])[CH3:39])[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[C:27]([OH:34])[C:26]=3[CH2:35][CH2:36][CH3:37])=[CH:13][CH:14]=2)[CH:9]=1.[OH-].[Na+]>CO>[C:38]([C:11]1[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[C:27]([OH:34])[C:26]=2[CH2:35][CH2:36][CH3:37])=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[C:8]([O:7][CH2:6][CH2:5][CH2:4][C:3]([OH:41])=[O:2])[CH:17]=[CH:16]2)(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 543662124-[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl)oxy]butanoic acid methyl ester

Product 1

HCID 135047804-[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]butanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.7 g of 4-[[8-acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester and 30 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 pH 3. The gummy precipitate was extracted with methylene chloride, the extract was washed with water, dried (magnesium sulfate) and concentrated in vacuo to an oil. The oil was triturated with hexane-ether to yield 1.4 g, m.p. 71°-75° C. (85%) of 4-[[8-acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]butanoic 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. washthe extract was washed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo to an oil
  7. customThe oil was triturated with hexane-ether

Sources & evidence

ORD record
ord-5afd5b1d6b1b402dbefef6a0bc10cd85
Source dataset
uspto-grants-1985_09
Patent number
US04539419

Reaction notes

Loading…