Water → HCID 10125342, compound

HRID 1830649Notes

Reaction equation

HRID 1830649 reaction equation
CC1C=CC(S([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([OH:28])[CH:24]=4)[CH:19]=3)=[C:14]([O:29][CH3:30])[CH:13]=2)(=O)=O)=CC=1.[OH-].[K+].O>C(O)C>[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([OH:28])[CH:22]=[CH:21]3)=[C:14]([O:29][CH3:30])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22048156HCID 22048156, compound

Product 1

HCID 10125342HCID 10125342, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(6-hydroxy-2-naphthyl)-3-methoxyphenyl 4-methylbenzenesulfonate (1.74 g, 4.05 mmol), potassium hydroxide (5 g), water (85 mL), and ethanol (85 mL) was stirred at 90° C. for 2 hr. The reaction was cooled to room temperature and concentrated to 50% volume, neutralized with acetic acid, and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, evaporation of the solvent, and purification by silica column (25% ethyl acetate-hexanes) yielded 1.01 g (94%) of the title compound as a tan solid. A sample was further purified by preparative reverse phase HPLC to yield a tan solid: mp 152–154° C.;

Workup

  1. concentrationconcentrated to 50% volume
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporation of the solvent, and purification by silica column (25% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-fc9b9b26115c48a59be1cb2fc58a01f9
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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