5-Chloro-2-hydroxy-4-methoxybenzaldehyde → HCID 68725341, compound

HRID 493202Notes

Reaction equation

HRID 493202 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:13]([Mg]Cl)([CH3:15])[CH3:14]>C1COCC1>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([OH:10])=[C:6]([CH:7]([OH:8])[CH:13]([CH3:15])[CH3:14])[CH:9]=1

Participants

4

Reactant 2

HCID 552533435-Chloro-2-hydroxy-4-methoxybenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 68725341HCID 68725341, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (0.845 g, 4.53 mmol) was dissolved in 10 mL of abs. THF and treated at −15° C. with iPrMgCl (4.98 mL of 2M [THF], 2.2 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, drying over sodium sulfate, and evaporation of the solvents left 1.090 g of the title compound as light brown oil, almost perfectly pure according to TLC and NMR.

Workup

  1. dissolutionwas dissolved in 10 mL of abs
  2. additionCareful pouring
  3. extractionice/NH4Cl, twofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. waitleft 1.090 g of the title compound as light brown oil

Sources & evidence

ORD record
ord-3d3df185e88a431bb244bc6bd2319b6e
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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