Hydrochloric Acid → 4-Methyloxybenzyl chloride

HRID 27600Notes

Reaction equation

HRID 27600 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:9].[CH2:10]=O>C1C=CC=CC=1>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([CH2:10][Cl:9])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 7519Anisole

Product 1

HCID 699934-Methyloxybenzyl chlorideYield 65.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
2 °C

Procedure

A solution comprising 108.1 grams of anisole in 450 ml of benzene was cooled to 2° C. and then saturated with gaseous hydrogen chloride for a period of 3 hours at a maximum temperature of 5° C. Then 38.6 grams of paraformaldehyde was added thereto at 20° C. and, following the addition, the reaction mixture was heated to 45° C. and maintained thereat for 1 hour and again cooled to 20° C. Following, gaseous hydrogen chloride was introduced for an additional 5 hours. Next, the aqueous layer was separated and the benzene solution washed with a saturated solution of calcium chloride in eight 150 ml portions and dried over magnesium sulfate. The residue was distilled in vacuum to yield 102.7 grams (65.7%) of 4-methoxybenzyl chloride, b.p. 108°-110° C./12 Torr.

Workup

  1. customat 20° C.
  2. additionthe addition
  3. temperaturethe reaction mixture was heated to 45° C.
  4. temperaturemaintained
  5. temperatureagain cooled to 20° C
  6. customNext, the aqueous layer was separated
  7. washthe benzene solution washed with a saturated solution of calcium chloride in eight 150 ml portions
  8. dry with materialdried over magnesium sulfate
  9. distillationThe residue was distilled in vacuum

Sources & evidence

ORD record
ord-dc89d07457d7424a831d2290891a75fd
Source dataset
uspto-grants-1980_09
Patent number
US04221919

Reaction notes

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