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

HRID 1981987Notes

Reaction equation

HRID 1981987 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:38](=[O:40])[CH3:39])[C:10]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][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:11][CH:12]=2)[CH:7]=1.[OH-].[Na+]>CO>[C:38]([C:9]1[C:10]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][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:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[C:6]([O:5][CH2:4][C:3]([OH:41])=[O:2])[CH:15]=[CH:14]2)(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13504774[[8-Acetyl-7-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-naphthalenyl]oxy]acetic acid methyl ester

Product 1

HCID 13504775[[8-Acetyl-7-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-naphthalenyl]oxy]acetic acidYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.2 g of [[8-acetyl-7-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-naphthalenyl]oxy]acetic acid methyl ester and 21 ml of 1N sodium hydroxide in 42 ml of methanol was stirred at reflux for 1 hour. The methanol was removed in vacuo and the aqueous solution was washed with ethyl acetate. The aqueous layer was acidified with 3N hydrochloric acid to pH 3 and the oil was extracted with chloroform. The extract was dried (magnesium sulfate) and concentrated to give an oil which was triturated with ether-cyclohexane and filtered to yield 0.85 g, mp 101°-104° C. (73%) of [[8-acetyl-7-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-naphthalenyl]oxy]acetic acid.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe methanol was removed in vacuo
  3. washthe aqueous solution was washed with ethyl acetate
  4. extractionthe oil was extracted with chloroform
  5. dry with materialThe extract was dried (magnesium sulfate)
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas triturated with ether-cyclohexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c35693ef7e1f444986e01dafae0d115c
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

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