Palmitoyl chloride → HCID 12800039, compound

A stirred solution of ethyl 3-amino-2-methylbenzoate (17.9 g) in chloroform (150 ml), containing triethylamine (15 ml), was treated with a solution of n-hexadecanoyl chloride (28 g) in chloroform (50 ml), during 30 minutes. The temperature of the reaction mixture was maintained at 0°-10° C. during the addition by ice cooling. The mixture was then refluxed for 90 minutes, washed with water (2×150 ml) and was dried over magnesium sulphate. The solvent was removed in vacuo to give a white solid, which was recrystallised from ethanol. The solid was dissolved in warm ethanol (500 ml) and the solution was treated with sodium hydroxide (10 g) in water (50 ml). The mixture was then refluxed for one hour and was poured onto a mixture of crushed ice and dilute hydrochloric acid (150 ml of strength 2N). The solid was collected and was recrystallised from ethanol (1000 ml) to give 3-(n-hexadecanamido)-2-methylbenzoic acid (28 g), in the form of a white solid, m.p. 163°-165° C.

1. temperatureThe temperature of the reaction mixture was maintained at 0°-10° C. during the addition by ice cooling
2. temperatureThe mixture was then refluxed for 90 minutes
3. washwashed with water (2×150 ml)
4. dry with materialwas dried over magnesium sulphate
5. customThe solvent was removed in vacuo
6. customto give a white solid, which
7. customwas recrystallised from ethanol
8. dissolutionThe solid was dissolved in warm ethanol (500 ml)
9. additionthe solution was treated with sodium hydroxide (10 g) in water (50 ml)
10. temperatureThe mixture was then refluxed for one hour
11. additionwas poured onto a mixture of crushed ice and dilute hydrochloric acid (150 ml of strength 2N)
12. customThe solid was collected
13. customwas recrystallised from ethanol (1000 ml)

ORD record

ord-4ab0214175c444cc85d46c7677f246f1

Source dataset

uspto-grants-1985_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04493843