Isobutanol → 4-Benzyloxy-2-ethyl-3-methylbenzohydrazide

HRID 453404Notes

Reaction equation

HRID 453404 reaction equation
C(O)C(C)C.[OH-].[NH3+:7][NH2:8].[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[C:19]([CH2:27][CH3:28])[C:18]=1[CH3:29])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(O)C>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([NH:7][NH2:8])=[O:22])=[C:19]([CH2:27][CH3:28])[C:18]=1[CH3:29])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 44558531Aminoammonium hydroxideHCID 67390959Methyl 4-benzyloxy-2-ethyl-3-methylbenzoate

Product 1

HCID 673915534-Benzyloxy-2-ethyl-3-methylbenzohydrazide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

20 ml of 2-propanol and 10 ml of isobutanol (2-methylpropan-1-ol) and also 20.0 ml of hydrazinium hydroxide are added to 17.5 g of methyl 4-benzyloxy-2-ethyl-3-methylbenzoate (C1). The reaction mixture is subsequently heated under reflux for 18 h overnight. After cooling, a further 30 ml of 2-propanol are added to the solution, which is subsequently stirred at room temperature for 30 min. The precipitate is filtered off with suction, and the filter cake is rinsed a number of times with a little 2-propanol. The product is subsequently recrystallised from 2-propanol, and the precipitate obtained is dried overnight in vacuo, giving 12.3 g of the title compound as a colourless, amorphous solid having a melting point of 179° C.; MS: 284.2 (M+); TLC: Rf=0.27 (ethyl acetate/ethanol 97:3 parts by volume).

Workup

  1. temperatureThe reaction mixture is subsequently heated
  2. temperatureunder reflux for 18 h overnight
  3. temperatureAfter cooling
  4. filtrationThe precipitate is filtered off with suction
  5. washthe filter cake is rinsed a number of times with a little 2-propanol
  6. customThe product is subsequently recrystallised from 2-propanol
  7. customthe precipitate obtained
  8. customis dried overnight in vacuo

Sources & evidence

ORD record
ord-ca618904c5b146ccbe4015ff9005f0eb
Source dataset
uspto-grants-2013_07
Patent number
US08492440B2

Reaction notes

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