Sodium Hydroxide → HCID 68650364, compound

HRID 402257Notes

Reaction equation

HRID 402257 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[O:25][CH2:24][CH2:23][CH2:22][C:21]([C:26]([O:28]CC)=[O:27])=[CH:20][C:19]=3[CH:31]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[O:25][CH2:24][CH2:23][CH2:22][C:21]([C:26]([OH:28])=[O:27])=[CH:20][C:19]=3[CH:31]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68650280HCID 68650280, compound

Product 1

HCID 68650364HCID 68650364, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 8-[4-(2-butoxyethoxy)phenyl]-3,4-dihydro-1-benzoxocin-5-carboxylate (527 mg) was dissolved in THF (40 ml) and methanol (40 ml). Aqueous 1N sodium hydroxide solution (12.4 ml) was added to the solution and the resulting solution was stirred overnight. After neutralization with 1N hydrochloric acid at 0° C., the solution was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from hexane-ethyl acetate to obtain colorless crystals of 8-[4-(2-butoxyethoxy)phenyl]-3,4-dihydro-2H-1-benzoxocin-5-carboxylic acid (160 mg).

Workup

  1. extractionAfter neutralization with 1N hydrochloric acid at 0° C., the solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-98dd5100b15644ff844c25a86c80bd28
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

Loading…