Methanol → (3-Methoxy-2-methylphenyl)methanol

HRID 730167Notes

Reaction equation

HRID 730167 reaction equation
[Li+].[BH4-].Cl[Si](C)(C)C.[CH3:8][O:9][C:10]1[C:11]([CH3:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=[O:14].CO>O1CCCC1>[CH3:8][O:9][C:10]1[C:11]([CH3:19])=[C:12]([CH2:13][OH:14])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 70214833-Methoxy-2-MethylBenzoic Acid

Product 1

HCID 15578709(3-Methoxy-2-methylphenyl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of LiBH4 (2.62 g; 120 mmol) in tetrahydrofuran (60 mL) was slowly added, via syringe, chlorotrimethylsilane (30.1 mL; 241 mmol). After stirring for 10 minutes, 3-methoxy-2-methylbenzoic acid (10.0 g, 60 mmol) was added in small portions. The mixture was stirred at ambient temperature for 18 hours. The mixture was cooled in an ice bath and methanol was slowly added until bubbling ceased and the solution turned clear. The reaction solution was evaporated to dryness. The residue was dispersed in dichloromethane and water. The phases were separated. The aqueous phase was basified with NaOH solution to pH 9-10 extracted with dichloromethane. The extracts were combined, dried over MgSO4, and evaporated to give (3-methoxy-2-methylphenyl)methanol 25, 9.10 g, 99% yield.

Workup

  1. additionwas slowly added, via syringe
  2. stirringThe mixture was stirred at ambient temperature for 18 hours
  3. temperatureThe mixture was cooled in an ice bath
  4. customuntil bubbling
  5. customThe reaction solution was evaporated to dryness
  6. additionThe residue was dispersed in dichloromethane
  7. customThe phases were separated
  8. extractionextracted with dichloromethane
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-aa60eb022a804cffb0eea476434e0cbf
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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