Water → (3-methoxy-4-methylphenyl)methanol

HRID 2368909Notes

Reaction equation

HRID 2368909 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6](O)=[O:7].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 815794-Methyl-m-anisic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11744818(3-methoxy-4-methylphenyl)methanolYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-4-methyl-benzoic acid (20.0 g, 0.12 mol) in dry THF (200 mL) at 0° C., LiAlH4 (6.9 g) was slowly added. The reaction was warmed to room temperature and stirred overnight. Water (20 mL) was slowly added at 0° C., and then 15% aqueous NaOH solution (50 mL) was added. The mixture was filtered, and the filtrate was extracted with ethyl acetate (3×100 mL). The combined extracts were dried over MgSO4, filtered and evaporated to give the title compound as pale yellow oil (16.0 g). 1H NMR (CDCl3): δ 7.13 (d, 1H), 6.85-6.79 (m, 2H), 4.64 (s, 2H), 3.84 (s, 3H), 2.21 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate was extracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6882b78c4e414d319d98e24f1e9b4c46
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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