Water → HCID 10495070, compound

HRID 2397058Notes

Reaction equation

HRID 2397058 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:10]([CH2:12][CH2:13][CH2:14]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:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:10]([CH2:12][CH2:13][CH2:14][Cl:3])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12679HexamethylphosphoramideHCID 24386Thionyl ChlorideHCID 18986932HCID 18986932, compound

Product 1

HCID 10495070HCID 10495070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.22 ml of thionyl chloride was added to a solution of 3.24 g of 3-[5-chloro-2-(2-phenylethoxy)phenyl]propanol and 5 ml of hexamethylphosphoric triamide in 25 ml of tetrahydrofuran under ice-cooling and 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, 3.21 g of crude 4-chloro-2-(3-chloropropyl)-1-(2-phenylethoxy)benzene was obtained. This compound was not purified any more but used in the subsequent reaction.

Workup

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

Sources & evidence

ORD record
ord-d4192624760c409e9d03e1ec3a7e654e
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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