Sodium Hydroxide → HCID 13505608, compound

HRID 2290434Notes

Reaction equation

HRID 2290434 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:35](=[O:37])[CH3:36])[C:10]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[C:26]([Cl:27])=[CH:25][C:24]([C:28](=[O:30])[CH3:29])=[C:23]([OH:31])[C:22]=3[CH2:32][CH2:33][CH3:34])=[CH:11][CH:12]=2)[CH:7]=1.[OH-].[Na+]>CO>[C:35]([C:9]1[C:10]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([C:28](=[O:30])[CH3:29])=[C:23]([OH:31])[C:22]=2[CH2:32][CH2:33][CH3:34])=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[C:6]([O:5][CH2:4][C:3]([OH:38])=[O:2])[CH:15]=[CH:14]2)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13505607HCID 13505607, compound

Product 1

HCID 13505608HCID 13505608, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.3 g of [[8-acetyl-7-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]-2-naphthalenyl]oxy]acetic acid methyl ester, 48 ml of methanol and 24 ml of 1N sodium hyroxide was stirred at reflux for one hour and 20 minutes. The methanol was removed in vacuo the aqueous solution was acidified to pH 3. The sticky solid was extracted with chloroform, washed with water, dried over magnesium sulfate and concentrated in vacuo to give an oil which was crystallized from ether to yield 0.93 g (78%) of [[8-Acetyl-7-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]-2-naphthalenyl]oxy]acetic acid, mp 132°-134° C.

Workup

  1. temperatureat reflux for one hour and 20 minutes
  2. customThe methanol was removed in vacuo the aqueous solution
  3. extractionThe sticky solid was extracted with chloroform
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas crystallized from ether

Sources & evidence

ORD record
ord-191acba4161c42c0adb533d59a1f5da2
Source dataset
uspto-grants-1986_10
Patent number
US04616091

Reaction notes

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