Hydrochloric Acid → Dibenz(c,e)oxepin-5(7H)-one

HRID 2119740

Reaction equation

HRID 2119740 reaction equation
[BH4-].[Na+].[C:3]12[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=O)[O:7][C:5](=[O:6])[C:4]1=[CH:16][CH:17]=[CH:18][CH:19]=2.Cl>CN(C=O)C.O>[CH:19]1[C:3]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][O:7][C:5](=[O:6])[C:4]=2[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 72794Diphenic anhydrideHCID 4311764Sodium borohydride

Product 1

HCID 4613402Dibenz(c,e)oxepin-5(7H)-oneYield 75.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

9.0 g (0.24 mol) of sodium borohydride were added in portions at 5° C. in the course of 10 min to a suspension of 50.0 g (0.22 mol) of diphenic anhydride in 220 ml of DMF. After stirring at RT for 1 h, the reaction mixture was poured onto 220 ml of 6 M hydrochloric acid, diluted with 750 ml of water and stirred for 2 h. The deposited precipitate was filtered off with suction and 35.0 g of 7H-dibenzo[c,e]oxepin-5-one were obtained; m.p. 131° C.

Workup

  1. stirringstirred for 2 h
  2. filtrationThe deposited precipitate was filtered off with suction

Sources & evidence

ORD record
ord-d2e8e7ec6a634f089861a868b6a4d799
Source dataset
uspto-grants-2004_02
Patent number
US06686395B2

Linked notes

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