2-Ethylhexanol → HCID 19003306, compound

HRID 1654562Notes

Reaction equation

HRID 1654562 reaction equation
Cl.[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19](Cl)=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1.[CH2:26]([CH:28]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:29][OH:30])[CH3:27].C(N(CC)CC)C.[K+].[Br-]>C(Cl)Cl.O.CN(C)C=O>[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19]([O:30][CH2:29][CH:28]([CH2:26][CH3:27])[CH2:31][CH2:32][CH2:33][CH3:34])=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1

Participants

8

Reactant 4

HCID 77202-EthylhexanolHCID 8471TriethylamineHCID 253877Potassium BromideHCID 131718103HCID 131718103, compound

Product 1

HCID 19003306HCID 19003306, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 5.0 g (0.013 mol) of the acid chloride of Example 2, 1.7 g (0.013 mol) 2-ethylhexanol and 50 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 2.8 g (0.028 mol) triethylamine in 5 ml methylene chloride. This addition produced an exotherm of about 10° C. The reaction was then refluxed for 1 hour. The mixture was cooled and transferred to a separatory funnel with 100 ml methylene chloride and 250 ml water. The ensuing emulsion was filtered, put back in the funnel and the phases separated. The organic phase was extracted with 50 ml water and 50 ml 5% sodium bicarbonate. The organic solution was dried with anhydrous magnesium sulfate and the solvent stripped using aspirator and high vacuum. Liquid chromatographic analysis of the white solid product indicated the presence of two components. The material was redissolved in methylene chloride and extracted with two 50 ml portions of 5% sodium hydroxide. The organic solution was again dried and stripped and the residue recrystallized from 80/20 ethanol/water. After isolation and drying, 1.5 g of slightly yellow product were obtained (melting 129°-131° C.). The infrared spectrum (KBr pellet) showed the carbonyl absorption at 1720 cm-1 (imide and ester). The NMR spectrum showed the anticipated aromatic ring (7.7-7.9 ppm, doublet, 1H; 8.2-8.5, multiplet, 2H) and the 2-ethylhexyl and HALS groups [4.4-4.9 ppm, multiplet, 1H; 4.2-4.3 ppm, doublet, 1H; 0.7-2.3 ppm, several multiplets including two singlets (1.2 and 1.3 ppm )].

Workup

  1. customInto a 125 ml reaction flask
  2. customequipped with a magnetic stirrer
  3. customthermometer, condenser and nitrogen atmosphere were placed
  4. additionThis addition
  5. customproduced an exotherm of about 10° C
  6. temperatureThe reaction was then refluxed for 1 hour
  7. temperatureThe mixture was cooled
  8. filtrationThe ensuing emulsion was filtered
  9. customthe phases separated
  10. extractionThe organic phase was extracted with 50 ml water and 50 ml 5% sodium bicarbonate
  11. dry with materialThe organic solution was dried with anhydrous magnesium sulfate
  12. dissolutionThe material was redissolved in methylene chloride
  13. extractionextracted with two 50 ml portions of 5% sodium hydroxide
  14. customThe organic solution was again dried
  15. customthe residue recrystallized from 80/20 ethanol/water
  16. customAfter isolation and drying
  17. custom1.5 g of slightly yellow product were obtained (melting 129°-131° C.)
  18. customthe carbonyl absorption at 1720 cm-1 (imide and ester)

Sources & evidence

ORD record
ord-38b66e3a9d014db4afa51d62a8fb91ef
Source dataset
uspto-grants-1995_04
Patent number
US05408008

Reaction notes

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