Hydrochloric Acid → HCID 22061198, compound

HRID 356575Notes

Reaction equation

HRID 356575 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

Procedure

5-Hydroxy-2-nitrobenzaldehyde (6.0 g) is dissolved in dry tetrahydrofuran (90 ml), and thereto is added dropwise with stirring vinylmagnesium bromide (2.3 equivalents) under -78° C. The mixture is gradually warmed, and after the reaction is completed, to the reaction mixture is added 1N hydrochloric acid. The mixture is extracted with ethyl acetate, and the organic layer is separated, washed with a saturated sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 1-(5'-hydroxy-2'-nitrophenyl)-2-propen-1-ol (5.09 g) as a yellow brown powder.

Workup

  1. temperatureThe mixture is gradually warmed
  2. extractionThe mixture is extracted with ethyl acetate
  3. customthe organic layer is separated
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e54f8f6d11554aee89e03fabc8574b96
Source dataset
uspto-grants-1998_11
Patent number
US05837673

Reaction notes

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