Sodium Hydroxide → HCID 15107359, compound

HRID 2108234Notes

Reaction equation

HRID 2108234 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][C:22]([O:30][CH3:31])=[C:23]([O:28][CH3:29])[CH:24]=3)[CH:19]=2)=[O:17])=[C:6]([CH2:32][CH2:33][CH3:34])[C:5]=1[OH:35].[OH-].[Na+]>CO.O1CCOCC1>[OH:35][C:5]1[C:6]([CH2:32][CH2:33][CH3:34])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][C:22]([O:30][CH3:31])=[C:23]([O:28][CH3:29])[CH:24]=3)[CH:19]=2)=[O:17])[CH:8]=[CH:9][C:4]=1[C:3]([OH:36])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15107358HCID 15107358, compound

Product 1

HCID 15107359HCID 15107359, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.2 g (0.0085 mole) of 2-hydroxy-4-[[6-(6,7-dimethoxy-2-naphthalenyl)-6-oxohexyl]oxy]-3-propylbenzoic acid methyl ester in 100 mL of methanol, 50 mL of dioxane and 34 mL (0.034 mole) of 1N sodium hydroxide was stirred at reflux for 8 hours. The reaction mixture was concentrated under reduced pressure, the residue was acidified and the product was extracted with ethyl acetate. The dried extract was concentrated and the crude product was recrystallized from a methanol and water mixture to give 3.48 g, mp 144°-146°, of 2-hydroxy-4-[[6-(6,7-dimethoxy-2-naphthalenyl)-6-oxohexyl]oxy-3-propylbenzoic acid.

Workup

  1. temperatureat reflux for 8 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated
  6. customthe crude product was recrystallized from a methanol and water mixture
  7. customto give 3.48 g, mp 144°-146°

Sources & evidence

ORD record
ord-0df0affeaa6343b8b57ba133e3eabb8a
Source dataset
uspto-grants-1990_06
Patent number
US04937371

Reaction notes

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