Methyl 2-chloro-4-(methylthio)benzoate → HCID 54209533, compound

HRID 1072900Notes

Reaction equation

HRID 1072900 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.CCOCC.Cl>[Cl:1][C:2]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 2

HCID 13961932Methyl 2-chloro-4-(methylthio)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 54209533HCID 54209533, compoundYield 103.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-chloro-4-(methylthio)benzoate (806 mg) was dropwise added to a suspension of lithium aluminum hydride (139 mg) in tetrahydrofuran (8 ml) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was diluted with ether and 1N hydrochloric acid (10 ml) was dropwise added. The resulting product was extracted three times with ether. The organic layers were combined, washed successively with 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 (725 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. additionwas dropwise added
  3. extractionThe resulting product was extracted three times with ether
  4. washwashed successively with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-adf549771a4c4af180d25b3d456f317d
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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