Diethyl Ether → HCID 67715310, compound

HRID 1451134Notes

Reaction equation

HRID 1451134 reaction equation
[C:1]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)O.[C:16](Cl)(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(OCC)C>N1C=CC=CC=1.CCCCCC>[Cl:13][C:12]([Cl:15])([Cl:14])[CH2:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11770936gamma-Linolenoyl ChlorideHCID 131848122,2,2-Trichloroethyl 2-hydroxybenzoate

Product 1

HCID 67715310HCID 67715310, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent2×

Procedure

--To a solution of 2,2,2-trichloroethyl salicylate (104 g) in dry pyridine (500 ml) at 0°-5° C. and under nitrogen was added (z,z,z)octadeca-6,9,12-trienoyl chloride (137.5 g) dropwise over a period of one hour. The reaction mixture was allowed to stir for twenty hours at room temperature and then the pyridine was removed in vacuo (25° C./0.5 mmHg). The residue was dissolved in diethyl ether (2000 ml) and water (1000 ml) and the resulting two phase system was shaken and acidified slowly to pH1 by addition of 2M hydrochloric acid. The diethyl ether layer was separated and washed with water (4×1000 ml), adding sodium chloride to break any emulsion that formed. After drying the organic layer (Na2SO4), the solvent was removed in vacuo to give an orange/brown oil. This was subjected to MPLC (Column size: 15 cm dia.×40 cm, Column packing: Matrex silica, pore size 60A, particle size 35-70 μm, Solvent: initially hexane, then 15% diethyl ether in hexane, Fraction size: 1000 ml). The requisite fractions were evaporated in vacuo to give 2,2,2-trichloroethyl-2-[(z,z,z) octadeca-6,9,12-trienoyl]benzoate. (189 g, 93% yield) as a pale yellow oil.

Workup

  1. customthe pyridine was removed in vacuo (25° C./0.5 mmHg)
  2. dissolutionThe residue was dissolved in diethyl ether (2000 ml)
  3. stirringwater (1000 ml) and the resulting two phase system was shaken
  4. additionacidified slowly to pH1 by addition of 2M hydrochloric acid
  5. customThe diethyl ether layer was separated
  6. washwashed with water (4×1000 ml)
  7. additionadding sodium chloride
  8. customthat formed
  9. dry with materialAfter drying the organic layer (Na2SO4)
  10. customthe solvent was removed in vacuo
  11. customto give an orange/brown oil
  12. customThe requisite fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-26511d48d1144448a9eb5a749c6d51f1
Source dataset
uspto-grants-1997_02
Patent number
US05603959

Reaction notes

Loading…