Hydrazine → 1,2-Dimethoxy-4,5-dimethylbenzene

HRID 1605200Notes

Reaction equation

HRID 1605200 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.[OH-].[K+].NN.COC1C=C(C)C=CC=1OC>C(O)COCCO>[CH3:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 681263,4-DimethoxytolueneHCID 821414,5-Dimethoxy-2-methylbenzaldehyde

Product 1

HCID 187953521,2-Dimethoxy-4,5-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

1.80 g of 6-methylveratraldehyde was treated with 2 g KOH, 1.4 ml 95% hydrazine, and 20 ml diethylene glycol in the manner described in the preparation of 3,4-dimethoxytoluene to give a quantitative yield of 4,5-dimethylveratrole as a cream colored solid. An analytical sample was sublimed (60°/0.05 mm Hg) to give a white powder, mp 41°-42°(Lit. 42.5°). Nmr (δ): 2.19 (s, 6H), 3.85 (s, 6H), 6.66 (s, 2H).

Sources & evidence

ORD record
ord-e4217c8f7c184f1798ee89878821e5c3
Source dataset
uspto-grants-1976_04
Patent number
US03950236

Reaction notes

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