Gamma-Butyrolactone → 4-Hydroxy-N-(9-octadecenyl)butyramide

HRID 1701721Notes

Reaction equation

HRID 1701721 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]1(=[O:25])[O:24][CH2:23][CH2:22][CH2:21]1>>[OH:25][CH2:20][CH2:21][CH2:22][C:23]([NH:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:24]

Participants

3

Reactant 2

HCID 7302Gamma-Butyrolactone2×HCID 5356789Oleylamine2×

Product 1

HCID 542069304-Hydroxy-N-(9-octadecenyl)butyramide

Conditions

Temperature
100 °C

Procedure

Oleylamine derived from fat was titrated and found to have an equivalent weight of 266.9 grams (theory=267.5 grams.). In a glass reaction vessel, 266.9 grams of the oleylamine were admixed with 86.1 grams of butyrolactone and the mixture heated to 100° C. on a steam bath until reaction was completed in a period of 2 hours. Greater than 95% conversion of the butyrolactone was achieved. The product upon cooling to room temperature produced a slightly off-white, hard, waxy solid which was found to be readily soluble in alcohols. IR=6.14 mu.

Workup

  1. temperatureThe product upon cooling to room temperature
  2. customproduced a slightly off-white, hard, waxy solid which

Sources & evidence

ORD record
ord-6ce7dccdde3e4655b3082b43ec0c64bd
Source dataset
uspto-grants-1980_03
Patent number
US04195096

Reaction notes

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