Sodium Hydroxide → 11-Hydroxy-11-methyl-6,11-dihydrodibenz[b,e]oxepin-2-carboxylic Acid

HRID 894217Notes

Reaction equation

HRID 894217 reaction equation
[OH:1][C:2]1([CH3:21])[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.[OH-].[Na+]>C(O)C>[OH:1][C:2]1([CH3:21])[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21162722Methyl 11-hydroxy-11-methyl-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Product 1

HCID 1292913211-Hydroxy-11-methyl-6,11-dihydrodibenz[b,e]oxepin-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 450 mg. of methyl 11-hydroxy-11-methyl-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate in 20 ml. of ethanol and add 20 ml. of 5% aqueous sodium hydroxide solution. Stir at room temperature for 1 hour. Evaporate the alcohol and dilute the residual sodium salt solution with 40 ml of water. Cool in an ice bath and acidify with 5N hydrochloric acid. Separate the solids by filtration and dry (yield 250 mg). Recrystallize from benzene to obtain the title product (yield 200 mg., m.p. 258°-258° C.).

Workup

  1. dissolutionDissolve 450 mg
  2. customEvaporate the alcohol
  3. additiondilute the residual sodium salt solution with 40 ml of water
  4. temperatureCool in an ice bath
  5. customSeparate the solids
  6. filtrationby filtration
  7. customdry (yield 250 mg)
  8. customRecrystallize from benzene

Sources & evidence

ORD record
ord-f8f3a18c970e4f9bbcacf8918a22c125
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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