N,N-Dimethylaniline → 5-(Chloromethyl)-1,2,3-trimethoxybenzene

HRID 323489Notes

Reaction equation

HRID 323489 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6]O.CN(C)C1C=CC=CC=1.S(Cl)([Cl:26])=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][Cl:26]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24386Thionyl ChlorideHCID 774493,4,5-Trimethoxybenzyl alcohol

Product 1

HCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 3,4,5-trimethoxybenzyl alcohol (1.0 g, 5.04 mmol) and N,N-dimethylaniline (0.904 g, 7.46 mmol) in dichloromethane (10 mL). Cool in an ice bath. Add dropwise thionyl chloride (0.904 g, 7.6 mmol). Warm to ambient temperature. After 1 hour, partition the reaction mixture between a 1 M aqueous hydrochloric acid solution and dichloromethane. Separate the layers and extract the organic layer with a saturated solution of sodium bicarbonate. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureCool in an ice bath
  2. custompartition the reaction mixture between a 1 M aqueous hydrochloric acid solution and dichloromethane
  3. customSeparate the layers
  4. extractionextract the organic layer with a saturated solution of sodium bicarbonate
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-2c7af49f80064e0e8616947b5f4d6232
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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