Water → 2-Benzyloxy-2'-methoxybenzophenone hydrazone

HRID 434206Notes

Reaction equation

HRID 434206 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:26][NH2:27].O>C(O)CCC.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=1[C:11](=[N:26][NH2:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 100872422-Benzyloxy-2'-methoxybenzophenone

Product 1

HCID 859607672-Benzyloxy-2'-methoxybenzophenone hydrazone

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension 2-benzyloxy-2′-methoxybenzophenone (13) (7.98 g, 0.025 mol) in hydrazine monohydrate (16 mL, 0.328 mol) and 1-butanol (25 mL) was heated to reflux overnight. After cooling to room temperature, the reaction mixture was poured into water saturated with salt and diluted with tetrahydrofuran. The organic phase which forms was separated, washed with water, saturated salt, and evaporated to dryness by rotary evaporation followed by application of high vacuum and mild heating. The resulting oil, 2-benzyloxy-2′-methoxybenzophenone hydrazone (14), which sometimes solidifies, still contains n-butanol and was used without further purification.

Workup

  1. temperatureto reflux overnight
  2. customThe organic phase which forms was separated
  3. washwashed with water, saturated salt
  4. customevaporated to dryness by rotary evaporation
  5. customstill contains n-butanol and was used without further purification

Sources & evidence

ORD record
ord-17e31e40c23645d983d7d7d3ec1b8a23
Source dataset
uspto-grants-2003_12
Patent number
US06670512B2

Reaction notes

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