Methane, dichloromethoxy- → HCID 19901373, compound

HRID 2372664Notes

Reaction equation

HRID 2372664 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([S:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:24][O:25]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]1([CH3:23])[CH:2]=[CH:3][C:4]([S:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:24]=[O:25])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 262323biphenyl-4-yl 4-methylbenzenesulfonate

Product 1

HCID 19901373HCID 19901373, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 21.06 g of 4-biphenylyl p-toluenesulphonate in 120 ml of dichloromethane was treated at -2° C. while stirring with 23.6 ml of titanium tetrachloride. The mixture was treated dropwise at the same temperature within 30 minutes with 9.63 ml of dichloromethyl methyl ether, stirred at room temperature for a further 1 hour and then poured on to ice. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with saturated sodium hydrogen carbonate solution and then with water, dried over sodium sulphate and concentrated. Recrystallization of the crude product obtained from 50 ml of ethyl acetate gave 11.65 g of 4'-(p-toluenesulphonyloxy)biphenyl-4-carboxaldehyde.

Workup

  1. additionwas treated at -2° C.
  2. additionpoured on to ice
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane
  5. washThe combined organic phases were washed with saturated sodium hydrogen carbonate solution
  6. dry with materialwith water, dried over sodium sulphate
  7. concentrationconcentrated
  8. customRecrystallization of the crude product
  9. customobtained from 50 ml of ethyl acetate

Sources & evidence

ORD record
ord-6e1b929f63f643f49a2cca76443a251f
Source dataset
uspto-grants-1992_03
Patent number
US05100577

Reaction notes

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