Oxygen → HCID 86754079, compound

HRID 1075700Notes

Reaction equation

HRID 1075700 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])(=[O:3])[CH3:2].[O:14]=O.[OH-].[Na+:17]>O.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][C:12]([O-:14])=[O:13])(=[O:3])[CH3:2].[Na+:17]

Participants

6

Reactant 3

HCID 977OxygenHCID 14798Sodium HydroxideHCID 53765498N-{2-[2-(2-Hydroxyethoxy)ethoxy]ethyl}acetamide

Product 1

HCID 86754079HCID 86754079, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

95.5 g of 8-acetylamino-3,6-dioxa-1-octanol were dissolved in 405 g of water, and 2.90 g of Pd/C (10% by weight) were added. The solution was heated to 70° C. and, while stirring vigorously, about 17 ml/min O2 were passed continously through the solution under atmospheric pressure for 14 h. Throughout the reaction, the pH was kept at 10 by continuously metering in a total of 105 g of 20% by weight aqueous NaOH. The remaining solution was then extracted with ethyl acetate in a perforator for 3 days. The aqueous phase was then distilled to dryness to leave 106 g (corresponding to 94% of theory) of sodium 8-acetylamino-3,6-dioxaoctanoate as viscous oil.

Workup

  1. customThroughout the reaction
  2. extractionThe remaining solution was then extracted with ethyl acetate in a perforator for 3 days
  3. distillationThe aqueous phase was then distilled to dryness

Sources & evidence

ORD record
ord-3c886546e77e41e59c2f078c820bc5ff
Source dataset
uspto-grants-1999_05
Patent number
US05907055

Reaction notes

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