Hydrochloric Acid → 7-(3,4-Methlenedioxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

HRID 1388034Notes

Reaction equation

HRID 1388034 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:11]=[CH:12][C:13]4[O:19][CH2:18][CH2:17][C:16]([C:20]([O-:22])=[O:21])=[CH:15][C:14]=4[CH:23]=3)=[CH:4][C:3]=2[O:2]1.[OH-].[Na+].Cl>CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:11]=[CH:12][C:13]4[O:19][CH2:18][CH2:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:14]=4[CH:23]=3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 184722037-(3,4-Methylenedioxy-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 184722047-(3,4-Methlenedioxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (5 ml) was suspended 7-(3,4-methylenedioxy-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (399 mg, 1.23 mmol), and to the mixture was added 1N sodium hydroxide solution (3.69 ml). The mixture was stirred at room temperature for 20 hours, and to the mixture was added 1N hydrochloric acid (3.69 ml). The mixture was concentrated under reduced pressure, and to the residue was added water. Insoluble materials were filtered, which were washed with water and diethylether and dried under reduced pressure to give 7-(3,4-methylenedioxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid(321 mg, 1.03 mmol, 84%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionto the residue was added water
  3. filtrationInsoluble materials were filtered
  4. washwhich were washed with water and diethylether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-752099da046a4eb6aecb440ab7c6d64d
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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