5-Chloro-2-hydroxy-4-methoxybenzaldehyde → HCID 68724734, compound

HRID 493211Notes

Reaction equation

HRID 493211 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].[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([OH:10])=[C:6]([CH:7]([OH:8])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 552533435-Chloro-2-hydroxy-4-methoxybenzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 68724734HCID 68724734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 5-chloro-2-hydroxy-4-methoxy-benzaldehyde (example 36, step 1, 1.050 g, 5.63 mmol) was dissolved in 15 mL of abs. THF and treated at −15° C. with PhMgBr (15.5 mL of 1M [THF], 2.7 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, followed by flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 1.39 g of the title compound as light brown oil.

Workup

  1. dissolutionwas dissolved in 15 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

Sources & evidence

ORD record
ord-3764a3de374849aa94b7d74bc8003a3b
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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