Hydrochloric Acid → Toluene, alpha-chloro-2,3,4-trimethoxy-

HRID 344708

Reaction equation

HRID 344708 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH2:5]O.[ClH:15]>O>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH2:5][Cl:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123571(2,3,4-Trimethoxyphenyl)methanol

Product 1

HCID 97491Toluene, alpha-chloro-2,3,4-trimethoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5.0 g (4.34 mmols) of 2,3,4-trimethoxybenzyl alcohol was dropwise added to 10 ml of conc. hydrochloric acid under stirring at 0° C. The mixture was stirred at 0° C. for further 5 minutes. After the reaction, water was added to the mixture followed by extraction of the solution with diethyl ether. The diethyl ether layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to afford 4.80 g of 2,3,4-trimethoxybenzyl chloride as a crude product.

Workup

  1. stirringThe mixture was stirred at 0° C. for further 5 minutes
  2. additionwas added to the mixture
  3. extractionfollowed by extraction of the solution with diethyl ether
  4. dry with materialThe diethyl ether layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a3a565d166b2461da24bbc4b59201e1e
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Linked notes

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