Benzene → 3-Chloromethyl-4-(4-methyl-phenoxy)-toluene

HRID 866592Notes

Reaction equation

HRID 866592 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:12]=2[CH2:13]O)=[CH:8][CH:7]=1.N1C=CC=CC=1.C1C=CC=CC=1>O>[Cl:3][CH2:13][C:12]1[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:11]=1[O:10][C:9]1[CH:20]=[CH:21][C:6]([CH3:5])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 54261585HCID 54261585, compound

Product 1

HCID 227679253-Chloromethyl-4-(4-methyl-phenoxy)-toluene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

36.5 Ml. of thionyl chloride are added dropwise at 10°-15° C. with stirring and cooling with ice to a solution of 110 g. of 2-(4-methyl-phenoxy)-5-methyl-benzyl alcohol in 78 ml. of pyridine. The mixture is stirred for an additional 1 hour at 10° C. and then diluted with 200 ml. of benzene. Then, 200 ml. of water are carefully added dropwise with ice-cooling. The aqueous phase is separated and the organic phase washed successively with dilute hydrochloric acid, water and saturated sodium bicarbonate solution. The aqueous phases are each extracted once more with benzene. The combined benzene extracts are dried over sodium sulfate and evaporated to dryness in vacuo and there is obtained 3-chloromethyl-4-(4-methyl-phenoxy)-toluene as an oil.

Workup

  1. temperaturecooling with ice to a solution of 110 g
  2. stirringThe mixture is stirred for an additional 1 hour at 10° C.
  3. additiondiluted with 200 ml
  4. temperaturecooling
  5. customThe aqueous phase is separated
  6. washthe organic phase washed successively with dilute hydrochloric acid, water and saturated sodium bicarbonate solution
  7. extractioneach extracted once more with benzene
  8. dry with materialThe combined benzene extracts are dried over sodium sulfate
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-bf103cfe1726442eb7d94744c3cbeb76
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

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