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

HRID 566010Notes

Reaction equation

HRID 566010 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][C:16]([C:20]([O:22]CC)=[O:21])=[CH:15][C:14]=3[CH:25]=2)=[CH:6][CH:5]=1)[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:14]=3[CH:25]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10759448Ethyl 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 105189987-(4-Ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (447.8 mg) in ethanol (20 ml) was added 2N sodium hydroxide (2.0 ml) at room temperature, and the mixture was stirred for 20 hours and concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (5 ml), and the mixture was extracted with ethyl acetate and concentrated. The resulting crystal was collected by filtration to give 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (380 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added 1N hydrochloric acid (5 ml)
  3. extractionthe mixture was extracted with ethyl acetate
  4. concentrationconcentrated
  5. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-216a47bc958f414eaa0656d831c71391
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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