Thionyl Chloride → HCID 67119342, compound

HRID 2076692Notes

Reaction equation

HRID 2076692 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:7]1[C:12]([CH2:13]O)=[CH:11][CH:10]=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:6]>C(Cl)Cl>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([CH2:13][Cl:3])[C:7]=2[CH2:5][CH3:6])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67119374HCID 67119374, compound

Product 1

HCID 67119342HCID 67119342, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After thionyl chloride (4 ml) was added to a solution of (2-ethyl-4′-methoxy-1,1′-biphenyl-3-yl)methanol (4.39 g, 17.9 mmol) obtained in Example (90-3) in methylene chloride (18 ml) under ice-cooling, the mixture was stirred at room temperature for 7 hours. The residue obtained by removing the solvent under reduced pressure was diluted with ethyl acetate and the mixture was successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 3′-(chloromethyl)-2′-ethyl-1,1′-biphenyl-4-yl methyl ether (3.32 g, yield: 71%).

Workup

  1. temperaturecooling
  2. customThe residue obtained
  3. customby removing the solvent under reduced pressure
  4. additionwas diluted with ethyl acetate
  5. washthe mixture was successively washed with water
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-130fbbe17d4943a09237778bbd7a064f
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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