Ammonium Hydroxide → 6-Hydroxycaproamide

HRID 380063Notes

Reaction equation

HRID 380063 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[O:8].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+].[NH4+:21].[OH-]>O>[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([NH2:21])=[O:1]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 62655Sodium PersulfateHCID 190319Hexanal, 6-hydroxy-

Product 1

HCID 118153906-HydroxycaproamideYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

5.26 Grams (45 mmols) of 6-hydroxyhexanal was charged to a 100 milliliter Schlenk flask and dissolved in 10 milliliters of deionized water by heating to 85-95° C. in a water bath. The resulting solution was charged to the Parr autoclave containing 0.484 grams of Na2S2O8 and 35 milliliters of NH4OH. The reactor was placed under 400 psi air, heated to 80° C. and a 500 psi air purge was established. The reaction was allowed to proceed for 3 hours. At that time, reaction conversion was virtually complete and 6-hydroxycaproamide was formed in 40% yield.

Workup

  1. additionThe resulting solution was charged to the Parr autoclave
  2. temperatureheated to 80° C.
  3. customa 500 psi air purge
  4. customAt that time, reaction conversion

Sources & evidence

ORD record
ord-0e35e80626804ba5b793668812997ba6
Source dataset
uspto-grants-2001_10
Patent number
US06300496B1

Reaction notes

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