Hydrochloric Acid → Erucoyl 1,3-propanediol

HRID 1699136Notes

Reaction equation

HRID 1699136 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[C:13](Cl)(=[O:35])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(OC(C)C)(C)C.Cl>C1COCC1.CN(C)C1C=CN=CC=1>[C:13]([CH:1]([OH:5])[CH2:2][CH2:3][OH:4])(=[O:35])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 104421,3-PropanediolHCID 5364502Erucoyl chloride

Product 1

HCID 86590002Erucoyl 1,3-propanediol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

1,3-Propanediol, 153 g (MW 76.1; 2 mol) is dissolved in 1 l of THF and, after addition of 60 g of triethylamine (MW 101.2, 0.6 mol) and 7.3 g of 4-dimethylaminopyridine (MW 122.2, 0.06 mol), equilibrated at 200° C. in a water bath. While stirring continuously, 178 g of erucoyl chloride (MW 357.0; 0.5 mol) in 500 ml of THF are slowly added dropwise so that the temperature in the reaction mixture does not exceed 30° C. The dropwise addition is followed by warming at 30° C. for 30 minutes and then addition of 1.5 1 of diisopropyl ether and 1.5 1 of 1N HCl. After vigorous shaking and phase separation, the upper ether phase is washed once again with 1% NaCl solution and evaporated in vacuo at 45° C. The residue is taken up in 2 l of hexane and cooled to −20° C. The white crystals are filtered off with suction and dried in vacuo. The yield of pure erucoyl-1,3-propanediol is 123 g (MW 396.7; 62%). The substance is pure by thin-layer chromatography (Rf value 0.3 in ether/pentane/acetic acid 200/200/2 parts by volume).

Workup

  1. customequilibrated at 200° C. in a water bath
  2. customdoes not exceed 30° C
  3. additionThe dropwise addition
  4. stirringAfter vigorous shaking
  5. customphase separation
  6. washthe upper ether phase is washed once again with 1% NaCl solution
  7. customevaporated in vacuo at 45° C
  8. temperaturecooled to −20° C
  9. filtrationThe white crystals are filtered off with suction
  10. customdried in vacuo

Sources & evidence

ORD record
ord-2005aeab0b7c47c0843c08aadd648399
Source dataset
uspto-grants-2002_02
Patent number
US06344576B1

Reaction notes

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