3,4,5-Trimethoxybenzaldehyde → 5-(2'-Chlorovinyl)-1,2,3-trimethoxy-benzene

HRID 845804Notes

Reaction equation

HRID 845804 reaction equation
[Cl-].[Cl:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[CH:33]=O>CS(C)=O.O1CCCC1>[Cl:2][CH:3]=[CH:33][C:32]1[CH:35]=[C:36]([O:40][CH3:41])[C:37]([O:38][CH3:39])=[C:30]([O:29][CH3:28])[CH:31]=1

Participants

6

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 178418339Butyllithium

Product 1

HCID 545254415-(2'-Chlorovinyl)-1,2,3-trimethoxy-benzeneYield 72.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 11.94 g of (chloromethyl)-triphenylphosphonium chloride in 85 ml of absolute dimethylsulfoxide and 170 ml of absolute tetrahydrofuran were added dropwise at 0° C., while stirring in an atmosphere of dry nitrogen, 21.5 ml of n-butyllithium solution. After stirring for 30 minutes a solution of 5.48 g of 3,4,5-trimethoxybenzaldehyde in 20 ml of absolute tetrahydrofuran was added dropwise. The mixture was stirred for 30 minutes at 0° C. and then allowed to warm to room temperature. After about 4 hours the reaction mixture was worked up in the manner described in Example 5e. Column chromatography of the raw product with petroleum ether/ether (2:1) yielded 4.64 g of the title compound.

Workup

  1. additionwere added dropwise at 0° C.
  2. additionwas added dropwise
  3. temperatureto warm to room temperature
  4. waitAfter about 4 hours the reaction mixture was worked up in the manner

Sources & evidence

ORD record
ord-5a2166f62c254c9180e529dcbeef73c3
Source dataset
uspto-grants-1988_07
Patent number
US04760087

Reaction notes

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