Sodium Hydroxide → 3-(Methylthio)benzyl alcohol

HRID 2414246Notes

Reaction equation

HRID 2414246 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7].COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2203293-(Methylthio)benzoic AcidHCID 16684438Red-Al

Product 1

HCID 122557423-(Methylthio)benzyl alcoholYield 68.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-methylsulfanyl-benzoic acid (38 g, 0.226 mol) in Toluene (500 mL) was added 200 mL of Red-Al® dropwise at 50° C. over 30 minutes. After stirring at room temperature for 3 hours, NaOH 10% (250 mL) was added while cooling with an ice-bath and then stirred overnight. The organic layer was separated and the water layer extracted twice with toluene (2×100 mL). The combined organic layers were dried (K2CO3), concentrated and distilled under reduced pressure to give the desired product (23.8 g, 68%). MS: 152,7 (M+131 ).

Workup

  1. temperaturewhile cooling with an ice-bath
  2. stirringstirred overnight
  3. customThe organic layer was separated
  4. extractionthe water layer extracted twice with toluene (2×100 mL)
  5. dry with materialThe combined organic layers were dried (K2CO3)
  6. concentrationconcentrated
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-5f1d2aedc20f4a61a4bf181c844a3dd9
Source dataset
uspto-grants-2004_11
Patent number
US06812228B2

Reaction notes

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