Sodium Hydroxide → HCID 19004518, compound

HRID 2225781Notes

Reaction equation

HRID 2225781 reaction equation
C[O:2][C:3](=[O:30])[C:4](=[O:29])[C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([O:13][CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[CH:7][C:6]=1[O:27][CH3:28].[OH-].[Na+]>CO.O1CCCC1.O>[CH3:12][O:11][C:10]1[CH:9]=[C:8]([O:13][CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH:7]=[C:6]([O:27][CH3:28])[C:5]=1[C:4](=[O:29])[C:3]([OH:30])=[O:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53951412HCID 53951412, compound

Product 1

HCID 19004518HCID 19004518, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,6-dimethoxy-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.5 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 dichloromethane-hexane provided 0.45 g of purified 2,6-dimethoxy-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid as a yellow solid, mp 154° C. with decomposition. Analysis Calculated for C22H20O7 : C, 66.66; H, 5.09.

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 dichloromethane-hexane

Sources & evidence

ORD record
ord-3919a25346e14e03b5163f303b8bf517
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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