Methanol → 2-Methoxy-3-methylbenzyl alcohol

HRID 1042352Notes

Reaction equation

HRID 1042352 reaction equation
[Li+].[BH4-].C[O:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[O:13][CH3:14].CO>CCOCC>[CH3:14][O:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][OH:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 13229229Methyl 2-methoxy-3-methylbenzoate

Product 1

HCID 536576772-Methoxy-3-methylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiBH4 (5.10 g, 0.23 mmol) was added to a solution of 2-methoxy-3-methyl-benzoic acid methyl ester (8.46 g, 47.00 mmol) in Et2O at 0° C. The reaction mixture was stirred for 5 minutes, MeOH (9.50 mL, 0.23 mmol) was added in a dropwise fashion. The reaction mixture was then stirred for 30 minutes, and was quenched into 1N NaOH. The resulting solution was extracted with Et2O (3×200 mL) and the combined organic phases were washed with brine (1×150 mL), dried over MgSO4 and concentrated to afford the title compound.

Workup

  1. stirringThe reaction mixture was then stirred for 30 minutes
  2. customwas quenched into 1N NaOH
  3. extractionThe resulting solution was extracted with Et2O (3×200 mL)
  4. washthe combined organic phases were washed with brine (1×150 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0d09a0335074675a496f017d1dd0309
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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