Chloroform → Benzylhydroxylamine

HRID 649248Notes

Reaction equation

HRID 649248 reaction equation
C(N(CC)CC)C.[OH-].[CH2:9]([NH:16][OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(Cl)(Cl)Cl>O>[CH2:9]([NH:16][OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8471TriethylamineHCID 86742113HCID 86742113, compound

Product 1

HCID 2794173Benzylhydroxylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.07 g of triethylamine is added at 0° C. while stirring to a solution of 7.87 g of O.benzylhydroxylamine hydroxide in a mixture of 50 ml of water and 50 if of CHCl3. The organic phase is separated out, washed with 3×50 ml of water, dried and evaporated under a vacuum. 6 g of O.benzylhydroxylamine base are obtained. The latter is added away from air in solution in 20 ml of MeOH to a solution of 2 g of 2-benzyl acrylic acid in 10 ml of MeOH. The mixture is refluxed for 7 days and concentrated under a vacuum. The oil obtained is dissolved in 100 ml of AcOEt and N NaOH is added until a pH 10 is reached. The aqueous phase is decanted and acidified with N HCl until a pH 1-2 is reached. The acid phase is extracted with AcOEt (2×50 ml), dried and evaporated under a vacuum. The oil obtained slowly crystallizes.

Workup

  1. customThe organic phase is separated out
  2. washwashed with 3×50 ml of water
  3. customdried
  4. customevaporated under a vacuum

Sources & evidence

ORD record
ord-c503b054dbc54aa1a2be1ab0d9be19a4
Source dataset
uspto-grants-1988_04
Patent number
US04738803

Reaction notes

Loading…