p-Cyanobenzyl alcohol → HCID 178513316, compound

HRID 2242231Notes

Reaction equation

HRID 2242231 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[OH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1>CO>[OH:3][NH:2][C:15](=[NH:16])[C:14]1[CH:17]=[CH:18][C:11]([CH2:10][OH:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

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

Product 1

HCID 178513316HCID 178513316, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (5.17 g, 75.0 mmol) and sodium bicarbonate (12.6 g, 150 mmol) were added to a solution of 4-hydroxymethyl-benzonitrile (5.0 g, 37.5 mmol) and methanol (65.0 mL). The reaction was heated to reflux for 12 hours. The reaction mixture was cooled to room temperature and the resulting slurry was filtered. The filtrate was concentrated in vacuo to give of the title compound (6.0 g, 48% yield) as an oily solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 12 hours
  3. filtrationthe resulting slurry was filtered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-012753b4a5fe4f13a48768fd5465b0de
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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