Hydrochloric Acid → HCID 29006117, compound

HRID 1712251

Reaction equation

HRID 1712251 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:3].[BH4-].[Na+].Cl>CO>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 224011524-Allyloxy-3-nitrobenzaldehyde

Product 1

HCID 29006117HCID 29006117, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 2.4 g of 4-allyloxy-3-nitrobenzaldehyde in 30 ml of methanol is cooled to 0° C. with stirring and subsequently admixed with 0.48 g of sodium borohydride in portions over 5 minutes. The reaction mixture is stirred further at 0° C. over 30 minutes, then poured onto cooled 2N HCl (100 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with water (100 ml), 1M sodium hydrogencarbonate solution (100 ml) and brine (100 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.12 (1:1 EtOAc-heptane); Rt=3.37.

Workup

  1. stirringThe reaction mixture is stirred further at 0° C. over 30 minutes
  2. additionpoured
  3. extractionextracted with tert-butyl methyl ether (2×100 ml)
  4. washThe organic phases are washed with water (100 ml), 1M sodium hydrogencarbonate solution (100 ml) and brine (100 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6ce231f443804a51b30a32f22725ea3a
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Linked notes

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