Hydrochloric Acid → 11-Methylene-6,11-dihydrodibenz[b,e]oxepin-2-carboxylic acid

HRID 894219Notes

Reaction equation

HRID 894219 reaction equation
[CH2:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([O:19]C)=[O:18])=[CH:16][C:3]1=2.C(O)C.[OH-].[Na+].Cl>O>[CH2:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:3]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 10106958Methyl 11-methylene-6,11-dihydrodibenz-[b,e]oxepin-2-carboxylate

Product 1

HCID 1292913311-Methylene-6,11-dihydrodibenz[b,e]oxepin-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve the residue of Step A above in 40 ml. of ethanol with warming. Cool and add 40 ml. of 20% aqueous sodium hydroxide solution. Allow to stand for 2 hour and strip away the alcohol. Dilute with water and acidify with 5 N hydrochloric acid. Separate the solids by filtration and dry to obtain the title product (yield 850 mg). Purify by recrystallization from ethanol (m.p. 255°-257° C.).

Workup

  1. temperatureCool
  2. additionadd 40 ml
  3. customSeparate the solids
  4. filtrationby filtration
  5. customdry

Sources & evidence

ORD record
ord-62a317d984554c198ba024376fbf0ee7
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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