Hydrochloric Acid → (4-Allyloxy-3-nitrophenyl)methanol

HRID 1176215

반응식

HRID 1176215 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 29006117(4-Allyloxy-3-nitrophenyl)methanol

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a3947d4449d345dc8657db91218cb8d1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

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