2-(Hydroxymethyl)octadecanoic acid → 2-Methylideneoctadecanoic acid

HRID 2049148Notes

Reaction equation

HRID 2049148 reaction equation
O[CH2:2][CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]([OH:6])=[O:5]>P(=O)(O)(O)O>[CH2:7]([C:3](=[CH2:2])[C:4]([OH:6])=[O:5])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 1

HCID 202182182-(Hydroxymethyl)octadecanoic acid

Product 1

HCID 3025852-Methylideneoctadecanoic acid

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

A 16.3 g sample of α-hydroxymethylstearic acid (0.0542 mole) and 6 drops of phosphoric acid (85%) are placed in a distillation flask and the mixture heated to 245°-255° C. in an oil bath under vacuum. The product, 2-hexadecyl acrylic acid, which distills over at 165°-175° C. at 0.1 mm (7.0 g) (43%), is recrystallized from acetone, m.p. 59°-63° C.

Workup

  1. temperaturethe mixture heated to 245°-255° C. in an oil bath under vacuum
  2. distillationThe product, 2-hexadecyl acrylic acid, which distills over at 165°-175° C. at 0.1 mm (7.0 g) (43%)
  3. customis recrystallized from acetone, m.p. 59°-63° C.

Sources & evidence

ORD record
ord-bb68d1a765144855a7842e97f2415e6c
Source dataset
uspto-grants-1980_04
Patent number
US04196300

Reaction notes

Loading…