Sodium Hydroxide → 7-(4-Chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

HRID 566006Notes

Reaction equation

HRID 566006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([O:20]CC)=[O:19])=[CH:13][C:12]=3[CH:23]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][C:12]=3[CH:23]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472211Ethyl 7-(4-chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 184723867-(4-Chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

To a solution of ethyl 7-(4-chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (400 mg) in tetrahydrofuran-ethanol (10-10 ml) was added 1N sodium hydroxide (2.0 ml) at room temperature, and the mixture was stirred for 42 hours and concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (15 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The resulting crystal was collected by filtration to give 7-(4-chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (342 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added 1N hydrochloric acid (15 ml)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-139d731b29fe4aaea956b89d4676d270
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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