Water → HCID 22388089, compound

HRID 1699916Notes

Reaction equation

HRID 1699916 reaction equation
N1C=CC=CC=1.S(Cl)([Cl:9])=O.[Cl:11][C:12]1[CH:19]=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[CH:16][C:13]=1[CH2:14]O.O>ClCCl>[Cl:11][C:12]1[CH:19]=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[CH:16][C:13]=1[CH2:14][Cl:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 22388433HCID 22388433, compound

Product 1

HCID 22388089HCID 22388089, compoundYield 106,483.797%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.5 ml) and thionyl chloride (0.18 mg) were successively added to a solution of 2-chloro-4-isopropoxybenzylalcohol (401 mg) in dichloromethane (2 ml) under ice-cooling, and the mixture was stirred for 1 hr. Water was added to the reaction mixture and the resulting product was extracted three times with hexane. The organic layers were combined, washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the objective compound (353 mg) as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe resulting product was extracted three times with hexane
  3. washwashed successively with 1N hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-09e3843cf1de40fcb8b861f0d708e3ed
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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