Veratryl alcohol → Veratryl chloride

HRID 1074546Notes

Reaction equation

HRID 1074546 reaction equation
[CH2:1](O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.S(Cl)([Cl:15])=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH2:1][Cl:15]

Participants

5

Reactant 3

HCID 7118Veratryl alcoholHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 81740Veratryl chlorideYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 235 g of veratryl alcohol in 1.4 liters of dry methylene chloride, 200 g of thionyl chloride was added dropwise while cooling with ice, and the mixture was stirred at room temperature overnight. The resulting dark brown reaction solution was poured into one liter of ice water. The pH of the solution was adjusted to 7.0 with sodium bicarbonate. The methylene chloride layer was separated, washed with water, dehydrated, and concentrated to dryness under vacuum to obtain 220 g of 3,4-dimethoxybenzyl chloride having a melting point of 50° to 51° C.

Workup

  1. temperaturewhile cooling with ice
  2. customThe methylene chloride layer was separated
  3. washwashed with water
  4. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-aeaedfde422d4a11b7e263cf38a932db
Source dataset
uspto-grants-1983_07
Patent number
US04393058

Reaction notes

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