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

HRID 660788Notes

Reaction equation

HRID 660788 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].S([O-])([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 (20 mL) is added LiAlH4 solution (26 mL, 1M in THF) dropwise and the mixture is stirred at RT for 1 h. The mixture is diluted with THF (80 mL) and cooled in an ice bath then saturated sodium sulfate solution (1 mL) is added dropwise. The mixture is filtered and the filtrate dried over magnesium sulfate and evaporated to give the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe mixture is filtered
  3. dry with materialthe filtrate dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-412cbb0f4bba4b0bb26f89b5353bd9ec
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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