Toluene → HCID 85381806, compound

HRID 2372093Notes

Reaction equation

HRID 2372093 reaction equation
[CH3:1][CH:2]([CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH:5]=O)[CH3:3].C(=O)(O)[O-].[Na+].Cl.[NH2:23][OH:24].C1(C)C=CC=CC=1>CO.O>[CH3:1][CH:2]([CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH:5]=[N:23][OH:24])[CH3:3]

Participants

7

Reactant 4

HCID 1140TolueneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 10878738HCID 10878738, compound

Product 1

HCID 85381806HCID 85381806, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

44.44 Grams (0.02 moles) of α-(1-methylethyl)-3,4-dimethoxybenzeneacetaldehyde prepared in example 2 are dissolved in 180 ml of methanol, then 17.64 g (0.21 moles) of sodium bicarbonate are added and, finally, 14.60 g (0.21 moles) of hydroxylamine hydrochloride are added portionwise in 30 minutes. After stirring for an additional 30 minutes, 150 ml of toluene and 150 ml of water are added and the layers are separated. The aqueous phase is discarded. The toluene phases are collected together, washed with 50 ml of water, dried over anhydrous sodium sulphate, filtered and evaporated to dryness under vacuum. The oily residue is purified by treatment with heptane obtaining 43.40 g of oxime with a yield of 91.4%. An oxime sample crystallized three times from tetrachloroethylene, shows m.p.=89° C.÷91° C. and a 1H-NMR spectrum showing characteristic resonance peaks at the following δ (expressed as p.p.m.): 0.8 (d, 3H); 1.01 (d, 3H); 2.07 (m, 1H); 3.04 (t, 1H); 3.87 (2s, 6H); 6.76 (m, 3H); 7.54 (d, 1H).

Workup

  1. customthe layers are separated
  2. customThe toluene phases are collected together
  3. washwashed with 50 ml of water
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness under vacuum
  7. customThe oily residue is purified by treatment with heptane obtaining 43.40 g of oxime with a yield of 91.4%
  8. customAn oxime sample crystallized three times from tetrachloroethylene
  9. customm.p.=89° C.÷91° C.

Sources & evidence

ORD record
ord-7a8a531654cc420dbc213e72fdfbf25b
Source dataset
uspto-grants-1992_03
Patent number
US05097058

Reaction notes

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