Methyl (11H-dibenzo[b,e][1,4]dioxepin-11-ylidene)acetate → HCID 12805670, compound

HRID 1462184Notes

Reaction equation

HRID 1462184 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[C:6]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=[O:4]>CO>[CH3:1][O:2][C:3]([CH2:5][CH:6]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=[O:4]

Participants

3

Reactant 1

HCID 54100731Methyl (11H-dibenzo[b,e][1,4]dioxepin-11-ylidene)acetate

Product 1

HCID 12805670HCID 12805670, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

27 g of 11-(methoxycarbonyl methylidene) dibenzo (b,e)-1,4-dioxepin (A or B isomer) were dissolved in 150 ml of methanol. The solution was purged with bubbling nitrogen, then 0.5 g of platinum dioxide were added. The mixture was hydrogenated under atmospheric pressure until the end of the absorption. The catalyst was filtered off and the methanol solution was half concentrated. The crystallization was started up, then the crystalline mixture was left at rest for 10 hours in a refrigerator. The crystalline mass was suctioned off and then dried under vacuum in a dessicator over phosphoric acid. There were obtained 13 g of a hydrogenated product (yield: 48%). The pure product, after recrystallization, melts at 72°-74° C.

Workup

  1. customThe solution was purged with bubbling nitrogen
  2. addition0.5 g of platinum dioxide were added
  3. customThe mixture was hydrogenated under atmospheric pressure until the end of the absorption
  4. filtrationThe catalyst was filtered off
  5. concentrationconcentrated
  6. customThe crystallization
  7. dry with materialdried under vacuum in a dessicator over phosphoric acid

Sources & evidence

ORD record
ord-becad8d1aab34bc4b6d2380372ff1a82
Source dataset
uspto-grants-1984_07
Patent number
US04459306

Reaction notes

Loading…