Sodium Hydroxide → HCID 19004386, compound

HRID 2225767Notes

Reaction equation

HRID 2225767 reaction equation
C[O:2][C:3](=[O:32])[C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][O:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:22][O:23][C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26][CH3:27])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[CH3:28][C:25]([CH3:29])([CH2:26][CH3:27])[C:24](=[O:30])[O:23][CH2:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[O:14][CH2:13][CH2:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:31])[C:3]([OH:32])=[O:2])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54063855HCID 54063855, compound

Product 1

HCID 19004386HCID 19004386, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[[2-[2-[(2,2-dimethyl-1-oxobutoxy)methyl]-6-methylphenoxy]ethyl]thio]-alpha-oxobenzeneacetic acid methyl ester (1.9 g) in warm methanol (10 mL) and tetrahydrofuran (5 mL) was treated with 1N sodium hydroxide (5 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. Purification was accomplished by chromatography on 60 g of silica gel using dichloromethane-diethyl ether-formic acid (50:50:1) to elute impurities followed by elution with diethyl ether-formic acid (99:1) to recover 1.1 g of pure 4-[[2-[2-[(2,2-dimethyl-1-oxobutoxy) methyl]-6-methylphenoxy]ethyl]thio]-alpha-oxobenzeneacetic acid as a yellow oil.

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. customPurification
  10. washto elute impurities
  11. washfollowed by elution with diethyl ether-formic acid (99:1)
  12. customto recover 1.1 g of pure 4-[[2-[2-[(2,2-dimethyl-1-oxobutoxy) methyl]-6-methylphenoxy]ethyl]thio]-alpha-oxobenzeneacetic acid as a yellow oil

Sources & evidence

ORD record
ord-cb1a2bd2a6b04792844dd20be6c87d0d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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