Ethyl Lactate → HCID 86690046, compound

HRID 628746Notes

Reaction equation

HRID 628746 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40].[C:41]([O:46]CC)(=[O:45])[CH:42]([CH3:44])[OH:43].C(=O)(O)[O-].[Na+]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40].[C:41]([O-:46])(=[O:45])[CH:42]([CH3:44])[OH:43]

Participants

4

Reactant 3

HCID 7344Ethyl Lactate2×HCID 516892Sodium BicarbonateHCID 656641Nonaethylene Glycol Monododecyl Ether

Product 1

HCID 86690046HCID 86690046, compoundYield 80.2%

Procedure

Polidocanol 41.32 g (70.9 mmol) Polidocanol, 21.07 g (178.4 mmol) ethyl lactate, 4.64 g Novozyme 435 and 1.00 g (11.9 mmol) sodium bicarbonate were added to a 100 mL 1-neck round bottom flask. The flask was then fitted to a rotary evaporator with the bath temperature set at 62° C. The pressure was slowly reduced to 15 mmHg under moderate rotation and the reaction mixture was held for 8 hours. Ethyl lactate (5.79 g, 49.0 mmol) was added to replenish the amount removed by distillation and the mixture was held an additional 16 hours at 62° C. and 15 mmHg. The round bottom flask was removed from the evaporator and the mixture was diluted with 20 mL petroleum ether. The solids were separated by vacuum filtration on a Buchner funnel with a #1 Whatman filter paper. The filtered solids were washed with 16 mL petroleum ether and the wash liquors were combined with the mother liquors. The combined filtrates were added to a 100 mL 1-neck round bottom flask and the flask was affixed to a rotary evaporator. The petroleum ether and excess ethyl lactate were distilled @15 mmHg with a bath temperature of 75-80° C. Upon completion of the distillation the pot was cooled and 38.19 g of Polidocanol lactate was obtained as a lightly colored waxy solid.

Workup

  1. customThe flask was then fitted to a rotary evaporator with the bath temperature
  2. customset at 62° C
  3. customremoved by distillation
  4. waitthe mixture was held an additional 16 hours at 62° C.
  5. customThe round bottom flask was removed from the evaporator
  6. additionthe mixture was diluted with 20 mL petroleum ether
  7. customThe solids were separated by vacuum filtration on a Buchner funnel with a #1 Whatman
  8. filtrationfilter paper
  9. washThe filtered solids were washed with 16 mL petroleum ether
  10. additionThe combined filtrates were added to a 100 mL 1-neck round bottom flask
  11. customthe flask was affixed to a rotary evaporator
  12. distillationThe petroleum ether and excess ethyl lactate were distilled @15 mmHg with a bath temperature of 75-80° C
  13. distillationUpon completion of the distillation the
  14. temperaturepot was cooled

Sources & evidence

ORD record
ord-5b9ef8e7f74042c98d3e8bca876aa261
Source dataset
uspto-grants-2016_04
Patent number
US09315446B2

Reaction notes

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