p-Cyanobenzyl alcohol → HCID 178513316, compound

HRID 1268919Notes

Reaction equation

HRID 1268919 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.Cl.[OH:12][NH2:13].C(=O)(O)[O-].[Na+]>CO>[OH:12][NH:13][C:7](=[NH:8])[C:6]1[CH:9]=[CH:10][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 160549p-Cyanobenzyl alcoholHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178513316HCID 178513316, compoundYield 124.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 25.0 g (150 mmol) of 4-(hydroxymethyl)benzonitrile, 20.8 g (300 mmol) of hydroxyamine hydrochloride and 50.4 g (600 mmol) of sodium bicarbonate in 250 mL of methanol was heated to reflux and stirred for 20 h. The reaction mixture was cooled to rt and filtered. The solid was washed with 100 mL of methanol. The combined methanol solution was concentrated to dryness to afford 31.0 g (99%) of the title compound: 1H NMR (400 Mhz, CD3OD) δ 4.63 (s, 2H), 7.39 (d, J=8.0, 2H), 7.62 (d, J=8.0, 2H).

Workup

  1. temperatureto reflux
  2. filtrationfiltered
  3. washThe solid was washed with 100 mL of methanol
  4. concentrationThe combined methanol solution was concentrated to dryness

Sources & evidence

ORD record
ord-9281f37e15d04a2c97607fa2ee28729c
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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