2-Hydroxy-4-methoxy-5-methylbenzaldehyde → 2-(1-Hydroxy-2-methyl-propyl)-5-methoxy-4-methyl-phenol

HRID 493209Notes

Reaction equation

HRID 493209 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[CH:13]([Mg]Cl)([CH3:15])[CH3:14]>C1COCC1>[OH:5][CH:4]([C:3]1[CH:6]=[C:7]([CH3:12])[C:8]([O:10][CH3:11])=[CH:9][C:2]=1[OH:1])[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 131668192-Hydroxy-4-methoxy-5-methylbenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 687253722-(1-Hydroxy-2-methyl-propyl)-5-methoxy-4-methyl-phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 2-hydroxy-4-methoxy-5-methyl-benzaldehyde (1.97 g, 11.86 mmol) was dissolved in 30 mL of abs. THF and treated at −15° C. with iPrMgCl (14.8 mL of 2M [THF], 2.5 eq.) and the mixture kept at this temperature for 0.5 h. Careful pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents left 2.45 g of the title compound as white crystals, almost perfectly pure according to TLC and NMR.

Workup

  1. dissolutionwas dissolved in 30 mL of abs
  2. additionCareful pouring
  3. extractionice/NH4Cl, twofold extraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  6. waitleft 2.45 g of the title compound as white crystals

Sources & evidence

ORD record
ord-79e9e3a0c31e4a02b668e10deefbf391
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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