Hydrochloric Acid → 4-(Chloromethyl)-2-methoxy-1-methylbenzene

HRID 1374994Notes

Reaction equation

HRID 1374994 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH2:6]O.[ClH:12].C(OC(C)C)(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH2:6][Cl:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 11744818(3-methoxy-4-methylphenyl)methanol

Product 1

HCID 116152544-(Chloromethyl)-2-methoxy-1-methylbenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-methoxy-4-methylbenzylalcohol (41.61 g), conc. hydrochloric acid (125 ml) and toluene (83 ml) was stirred at 90° C. for 1 hour. After cooling, ice-water (125 ml) and diisopropyl ether (80 ml) were added to the mixture, and the organic layer was separated, and the aqueous layer was extracted with diisopropyl ether (160 ml). The combined organic layer was washed with saturated sodium hydrogen carbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo to give 3-methoxy-4-methylbenzyl chloride (46.35 g) as an oil.

Workup

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with diisopropyl ether (160 ml)
  4. washThe combined organic layer was washed with saturated sodium hydrogen carbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-39ffb9a30e824374a9106730e09699e4
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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