Sodium Hydroxide → HCID 19004330, compound

HRID 2225776Notes

Reaction equation

HRID 2225776 reaction equation
C[O:2][C:3](=[O:28])[C:4](=[O:27])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[C:7]([Cl:26])[CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[Cl:11][C:9]1[CH:10]=[C:5]([C:4](=[O:27])[C:3]([OH:28])=[O:2])[CH:6]=[C:7]([Cl:26])[C:8]=1[O:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53777040HCID 53777040, compound

Product 1

HCID 19004330HCID 19004330, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,5-dichloro-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.6 g) in warm methanol (10 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (2 mL) and after 10 minutes the mixture was diluted with water and concentrated to remove the organic solvents. The residue was acidified with excess hydrochloric acid and extracted with dichloromethane containing a little tetrahydrofuran. The organic layer was washed with water, dried (Na2SO4), filtered and evaporated to give crude product. Crystallization from benzene-hexane provided 0.575 g of purified 3,5-dichloro-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid (6:1) molar benzene solvate as a colorless solid, mp 108°-110° C.

Workup

  1. concentrationconcentrated
  2. customto remove the organic solvents
  3. extractionextracted with dichloromethane containing a little tetrahydrofuran
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude product
  9. customCrystallization from benzene-hexane

Sources & evidence

ORD record
ord-c3e7fc6ddc6847e9a2fde3d4df5e2d65
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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