Gamma-Butyrolactone → N-Decyl-4-hydroxybutyramide

HRID 1701719Notes

Reaction equation

HRID 1701719 reaction equation
[CH2:1]([NH2:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12]1(=[O:17])[O:16][CH2:15][CH2:14][CH2:13]1>>[CH2:1]([NH:11][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 7302Gamma-Butyrolactone2×HCID 8916Decylamine

Product 1

HCID 11139345N-Decyl-4-hydroxybutyramide

Procedure

In a glass reaction vessel, 157.3 grams of decylamine was mixed with 86.1 grams butyrolactone, whereupon the temperature rose to about 150° C. Reaction was spontaneous, and greater than 95% conversion of the butyrolactone to product was achieved. Titration of the product indicated that only 0.4 weight percent free amine remained unreacted. The liquid product was cooled by pouring on a glass surface at room temperature, whereupon the product froze to a hard white, waxy solid. Titration of the remaining reaction mixture indicated that only 0.4 weight percent free amine remained after removal of product. IR=6.11 mu.

Workup

  1. customrose to about 150° C
  2. customReaction
  3. temperatureThe liquid product was cooled
  4. additionby pouring on a glass surface at room temperature, whereupon the product
  5. customTitration of the remaining reaction mixture
  6. customafter removal of product

Sources & evidence

ORD record
ord-26d2bb24483140a88169a6c1ff3f8e5d
Source dataset
uspto-grants-1980_03
Patent number
US04195096

Reaction notes

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