Thionyl Chloride → HCID 20513505, compound

HRID 1163986Notes

Reaction equation

HRID 1163986 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]O>N1C=CC=CC=1.C1C=CC=CC=1>[CH3:5][O:6][C:7]1[C:8]([CH2:9][Cl:3])=[CH:11][CH:12]=[CH:13][C:14]=1[O:15][C:16]1[C:17]([CH3:22])=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 13066663HCID 13066663, compound

Product 1

HCID 20513505HCID 20513505, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Procedure

Thionyl chloride (30 ml) and pyridine (1 drop) were added to a solution of 2-methoxy-3-(o-tolyloxy)benzyl alcohol (44.0 g) in benzene (150 ml). The mixture was refluxed under heating for 40 minutes and then evaporated. The residue was dissolved in diethyl ether, washed with aqueous sodium bicarbonate and water successively, dried over magnesium sulfate and then evaporated to give oily o-tolyl 2-methoxy-3-chloromethylphenyl ether (47.50 g).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 40 minutes
  3. customevaporated
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washwashed with aqueous sodium bicarbonate and water successively
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-e11600c4971343ab832d6dce32ee3a5d
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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