Water → HCID 18986900, compound

HRID 2397064Notes

Reaction equation

HRID 2397064 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15]O)[CH:11]=1.CN(C)P(=O)(N(C)C)N(C)C.O>O1CCCC1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][Cl:3])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12679HexamethylphosphoramideHCID 24386Thionyl ChlorideHCID 10756943HCID 10756943, compound

Product 1

HCID 18986900HCID 18986900, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.31 ml of thionyl chloride was added under ice-cooling to a solution of 0.86 g of 4-[5-chloro-2-(2-phenylethoxy)phenyl]butanol and 4 ml of hexamethylphosphoric triamide in 20 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water (100 ml), extracted with ethyl acetate, successively washed with water twice and a saturated aqueous solution of sodium hydrogencarbonate 4 times and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 0.91 g of crude 4-chloro-2-(4-chlorobutyl)-1-(2-phenylethoxy)benzene was obtained. This compound was not purified any more but used in the subsequent reaction.

Workup

  1. extractionextracted with ethyl acetate
  2. washsuccessively washed with water twice
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate 4 times and dried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e89637e637414536bcfda34b7cfd29be
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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