Hydrochloric Acid → HCID 22061198, compound

HRID 1953076Notes

Reaction equation

HRID 1953076 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:13]([Mg]Br)=[CH2:14].Cl>O1CCCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]([OH:8])[CH:13]=[CH2:14])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 22061198HCID 22061198, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

5-Hydroxy-2-nitrobenzaldehyde (60 g) is dissolved in dry tetrahyrofuran (90 ml) and thereto is added dropwise vinylmagnesium bromide (2.3 equivalents) with stirring at -78° C. The temperature of the reaction mixture is raised gradually. After completion of the reaction, 1N HCl is added to the reaction mixture, and the mixture is extracted with ethyl acetate, and the organic layer is separated, washed with an aqueous saturated saline solution, dried over sodium sulfate, and then distilled off the solvent. The residue is purified with a silica gel column chromatography to give 1-(5'-hydroxy-2'-nitrophenyl)-2-propen-1-ol (5.09 g) as yellowish brown powders.

Workup

  1. temperatureThe temperature of the reaction mixture is raised gradually
  2. additionis added to the reaction mixture
  3. extractionthe mixture is extracted with ethyl acetate
  4. customthe organic layer is separated
  5. washwashed with an aqueous saturated saline solution
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled off the solvent
  8. customThe residue is purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-251f261540a9468b8f73b3d13d99563d
Source dataset
uspto-grants-2000_09
Patent number
US06114529

Reaction notes

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