Sodium Sulfate → [2-(4-Methoxybenzyloxy)-5-methylphenyl]-methanol

HRID 1642642Notes

Reaction equation

HRID 1642642 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:5]2[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=2[CH2:3][OH:2])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 66756631Methyl 2-(4-methoxybenzyloxy)-5-methylbenzoate

Product 1

HCID 63325270[2-(4-Methoxybenzyloxy)-5-methylphenyl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(4-methoxybenzyloxy)-5-methylbenzoic acid methyl ester (7.32 g, 25.6 mmol) in THF at 0° C. is added LiAlH4 (1 M in THF, 26 mL, 26 mmol) dropwise and the mixture is stirred for 1 h. Na2SO4 (saturated, 1 mL) is added dropwise at 0° C. and let it sit for 15 min. More THF (80 mL) is added and it is filtered. The filtrate is then concentrated and EtOAc (100 mL) is added. The organic layer is washed with brine and dried with MgSO4. It is then concentrated to give the title compound.

Workup

  1. waitsit for 15 min
  2. filtrationit is filtered
  3. concentrationThe filtrate is then concentrated
  4. additionEtOAc (100 mL) is added
  5. washThe organic layer is washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationIt is then concentrated

Sources & evidence

ORD record
ord-dc693f0da3894dd4900d54b01ddb2e2e
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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