Hydrazine hydrate (1:1) → 1,1'-(Diazomethylene)bis(benzene)

HRID 2078676Notes

Reaction equation

HRID 2078676 reaction equation
C(O[C:14]1[CH:40]=[CH:39][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23](OCCCCCCCCCCCC)=[CH:22][CH:21]=2)=O)=[CH:16][CH:15]=1)CCCCCCCCCCC.O.[NH2:42][NH2:43]>C(O)CCCC>[C:17]1([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N+:42]=[N-:43])[CH:39]=[CH:40][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23432421HCID 23432421, compound

Product 1

HCID 612301,1'-(Diazomethylene)bis(benzene)

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A mixture of 4,4′-dihydroxybenzophenone (21.4 g, 100 mmol), 1-bromododecane (49.8 g, 200 mmol), K2CO3 (50 g) in 500 mL of DMF were heated with stirring at 120° C. for 60 hours. After the mixture was cooled to room temperature, 1 L of water was added. The solution was extracted with CH2Cl2 (4×500 mL). The combined organic layers were dried with MgSO4 and the most of the solvent removed under reduced pressure as a white solid formed. The solids were collected by filtration, washed with cold hexanes, and air dried to give 4,4′-didodecyloxybenzophenone (41.2 g, 75%). A mixture of 4,4′didodecyloxybenzophenone (20.6 g) and hydrazine monohydrate (20 mL) in 150 mL of pentanol were heated at reflux for 24 hours. After cooling to room temperature, a white solid precipitated which is collected by vacuum filtration, washed with 20 mL cold ethanol and air dried (19.4 g, 92%).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 24 hours
  3. customa white solid precipitated which
  4. filtrationis collected by vacuum filtration
  5. washwashed with 20 mL cold ethanol and air
  6. customdried (19.4 g, 92%)

Sources & evidence

ORD record
ord-fd649e2e87ed496789eb1970ca10706b
Source dataset
uspto-grants-2011_04
Patent number
US07928432B2

Reaction notes

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