Pyridine → 3,5-Dimethoxybenzyl chloride

HRID 1449063Notes

Reaction equation

HRID 1449063 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH2:10]O.N1C=CC=CC=1>CCOCC>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH2:10][Cl:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 697183,5-Dimethoxybenzyl alcohol

Product 1

HCID 27583953,5-Dimethoxybenzyl chlorideYield 86.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Over a period of 20 minutes a solution of 150 g (1.26 moles) of thionyl chloride in 0.65 l of ether was added to 100 g (0.59 moles) of 3,5-dimethoxybenzyl alcohol and 6.6 ml of pyridine in 1.35 l of ether. After stirring for 3 hr the solution containing the product was separated from the residual dark oil, concentrated, and the crude product was redissolved in 1 l of ether, washed with water (3×250 ml), dried (brine, magnesium sulfate), filtered, and reconcentrated to give a dark oil which was vacuum distilled: b.p. 115°-118° C. at 0.4 mm Hg. Upon standing, fractions containing the desired compound solidified to give 95.3 g (86%) of white solid, m.p. 43°-45° C.

Workup

  1. additioncontaining the product
  2. customwas separated from the residual dark oil
  3. concentrationconcentrated
  4. dissolutionthe crude product was redissolved in 1 l of ether
  5. washwashed with water (3×250 ml)
  6. dry with materialdried (brine, magnesium sulfate)
  7. filtrationfiltered
  8. customto give a dark oil which
  9. distillationdistilled
  10. additionfractions containing the desired compound

Sources & evidence

ORD record
ord-5f9f8762e071494489091338f78ae719
Source dataset
uspto-grants-1980_02
Patent number
US04188495

Reaction notes

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