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

HRID 1277209Notes

Reaction equation

HRID 1277209 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][C:15]([C:19]([O:21]CC)=[O:20])=[CH:14][C:13]=3[CH:24]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=3[CH:24]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472190Ethyl 7-(4-methylthiophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 184724727-(4-Methylthiophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of ethyl 7-(4-methylthiophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (132 mg) in ethanol-tetrahydrofuran (5 ml-5 ml) was added 1N sodium hydroxide (1.0 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 (2 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 under reduced pressure. The resulting crystal was collected by filtration to give 7-(4-methylthiophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (113 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added 1N hydrochloric acid (2 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 under reduced pressure
  7. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-fa1ab0e938aa48d3925195713db32af2
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

Loading…