Sodium Hydroxide → HCID 15337974, compound

HRID 1647500Notes

Reaction equation

HRID 1647500 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH:13]([OH:26])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=3)=[CH:10][C:9]=2[CH:27]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH:13]([OH:26])[CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=3)=[CH:10][C:9]=2[CH:27]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9907292HCID 9907292, compound

Product 1

HCID 15337974HCID 15337974, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-tert-Butyl-2-[1-hydroxy-2-(4-methoxycarbonylphenoxy)ethyl]benzofuran (112 g) obtained in Example 1 was dissolved in 1.5 liters of methanol, a solution of 24.3 g of sodium hydroxide dissolved in 400 ml of water was added thereto and the mixture was heated to reflux for 2 hours. The reaction mixture was concentrated in vacuo, ice water was added to the residue and the mixture was acidified with concentrated hydrochloric acid to give crystals. The crystals collected by filtration were dissolved in ethyl acetate, the solution was washed with water and dried over anhydrous magnesium sulfate followed by concentrating in vacuo whereupon the residue is crystallized. This was dried and recrystallized from acetonitrile to give 88.3 g of crystals. M.p. 175°-177° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 hours
  4. concentrationThe reaction mixture was concentrated in vacuo, ice water
  5. additionwas added to the residue
  6. customto give crystals
  7. filtrationThe crystals collected by filtration
  8. dissolutionwere dissolved in ethyl acetate
  9. washthe solution was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationby concentrating in vacuo whereupon the residue
  12. customis crystallized
  13. customThis was dried
  14. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-f236c6633afe444e86da2a7098d71c96
Source dataset
uspto-grants-1995_07
Patent number
US05432195

Reaction notes

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