Tetrahydrofuran → 6,11-Dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylic Acid

HRID 894200Notes

Reaction equation

HRID 894200 reaction equation
[OH:1][CH: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.O1CCCC1.[OH-].[Na+]>O>[OH:1][CH: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

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2769059Methyl 11-hydroxy-6,11-dihydrobenzo[c][1]benzoxepine-2-carboxylate

Product 1

HCID 129291446,11-Dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve 900 mg. of methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate in 20 cc. of tetrahydrofuran. Add 20 cc. 1 N aqueous sodium hydroxide. Stir at room temperature for 48 hours. Dilute with water and extract with ether. Acidify the aqueous fraction with hydrochloric acid and extract with ether. Evaporate the organic phase to obtain the title product (m.p. 275° C. dec.).

Workup

  1. dissolutionDissolve 900 mg
  2. additionAdd 20 cc
  3. extractionextract with ether
  4. extractionextract with ether
  5. customEvaporate the organic phase

Sources & evidence

ORD record
ord-06261300041049b7ae1e5f982962a19a
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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