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

HRID 894220Notes

Reaction equation

HRID 894220 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]([OH:19])=[O:18])=[CH:16][C:3]1=2>[Pd].C(O)C>[CH3:1][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

4

Reactant 1

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

Product 1

HCID 1292913411-Methyl-6,11-dihydrodibenz[b,e]oxepin-2-carboxylic AcidYield 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 514 mg of 11-methylene-6,11-dihydrodibenz[b,e]oxepin-2-carboxylic acid in 150 ml. of ethanol. Add 100 mg of 5% palladium on carbon catalyst. Hydrogenate at 20 psi for 30 minutes. Filter and strip the filtrate to dryness. Recrystallize the residue from isopropanol to obtain the title product (yield 365 mg, m.p. 224°-226° C.).

Workup

  1. filtrationFilter
  2. customRecrystallize the residue from isopropanol

Sources & evidence

ORD record
ord-5c4ef8f90bd149b48d2a71d8c3ea4744
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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