Sodium Hydroxide → HCID 19004284, compound

HRID 2225766Notes

Reaction equation

HRID 2225766 reaction equation
C[O:2][C:3](=[O:24])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[CH:15]1([O:14][CH2:13][CH2:12][S:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:23])[C:3]([OH:24])=[O:2])=[CH:10][CH:9]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54032469HCID 54032469, compound

Product 1

HCID 19004284HCID 19004284, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[[2-(cyclooctyloxy)ethyl]thio]-alpha-oxobenzeneacetic acid methyl ester (0.96 g) in warm methanol (10 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (3.5 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. Crystallization from diethyl ether-hexane provided 0.86 g of purified 4-[[2-(cyclooctyloxy)ethyl]thio]-alpha-oxobenzeneacetic acid as a yellow solid, mp 84°-85° 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 diethyl ether-hexane

Sources & evidence

ORD record
ord-b20ba4089ccb420ba2ea228275d556f8
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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