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

HRID 1828800Notes

Reaction equation

HRID 1828800 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:17]=[C:16]([S:18][CH3:19])[CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11]>O1CCCC1.C(OCC)C.Cl>[Cl:7][C:8]1[CH:17]=[C:16]([S:18][CH3:19])[CH:15]=[CH:14][C:9]=1[CH2:10][OH:11]

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

To a suspension of lithium aluminum hydride (139 mg) in tetrahydrofuran (8 ml) was added dropwise methyl 2-chloro-4-(methylthio)benzoate (806 mg) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was diluted with diethyl ether and 1N hydrochloric acid (10 ml) was added dropwise. The resulting product was extracted 3 times with diethyl ether. The organic layers were combined and washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 2-chloro-4-(methylthio)benzyl alcohol (725 mg) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-19b2a89483364920af1f0e09f2970600
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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