3,4-Dimethoxytoluene → 1,2-Dimethoxy-4-methyl-5-(2-cyano-3-methoxy-2-propenyl)benzene

HRID 26667

Reaction equation

HRID 26667 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:12][O:13][CH:14](OC)[C:15](=[CH2:18])[C:16]#[N:17]>C(Cl)Cl>[CH3:10][O:9][C:8]1[CH:7]=[C:6]([CH2:18][C:15]([C:16]#[N:17])=[CH:14][O:13][CH3:12])[C:5]([CH3:11])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 681263,4-DimethoxytolueneHCID 124234392-Dimethoxymethylacrylonitrile

Product 1

HCID 544881951,2-Dimethoxy-4-methyl-5-(2-cyano-3-methoxy-2-propenyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10 g. of 3,4-dimethoxytoluene and 9.6 g. of 2-dimethoxymethylacrylonitrile in 200 ml. of dry methylene chloride was added dropwise at 0°, 2.3 ml. (0.0197 mole) of stannic chloride. The reaction mixture was stirred for 6 hours at 20°-25°, diluted with 500 ml. of ether, and the resulting solution washed with a 5% sodium bicarbonate solution until the aqueous layer remained basic. The combined aqueous washings were backwashed with ether and the organic layers were then combined and dried (MgSO4). The solvent was then removed under reduced pressure leaving an off-white residue of crude 1,2-dimethoxy-4-methyl-5-(2-cyano-3-methoxy-2-propenyl)benzene.

Workup

  1. additiondiluted with 500 ml
  2. washof ether, and the resulting solution washed with a 5% sodium bicarbonate solution until the aqueous layer
  3. dry with materialdried (MgSO4)
  4. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-eaa1ae833ef0486bad04e17db3c6680f
Source dataset
uspto-grants-1979_04
Patent number
US04151196

Linked notes

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