Hydrochloric Acid → HCID 67689502, compound

HRID 258438Notes

Reaction equation

HRID 258438 reaction equation
[C:1]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)(=[O:5])[C@H:2]([CH3:4])[OH:3].C(N(CC)CC)C.C(Cl)Cl.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25].Cl>>[C:23]([O:3][C@@H:2]([CH3:4])[C:1]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5])(=[O:26])[CH:24]=[CH2:25]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 54079296HCID 54079296, compound

Product 1

HCID 67689502HCID 67689502, compoundYield 102%

Conditions

Temperature
-20 °C

Procedure

To a mixture of 10.1 g (58.5 mmol) of cyclohexyl (s)-(-)-lactate, 8.1 g (80.4 mmol) of triethylamine and ml of methylene chloride, 5.7 ml (70.2 mmol) of acryloyl chloride was added dropwise at a temperature of -20° C., and the mixture was stirred at -20° C. for 5.5 hours. On ice cooling, 1N hydrochloric acid was added to the reaction mixture to separate an organic layer, and an aqueous layer was extracted with methylene chloride. Organic layers were combined and washed with successive, saturated sodium bicarbonate solution, water, and saturated sodium chloride solution. The solution was dried over anhydrous magnesium sulfate and filtered, the solvent was distilled off, and 13.5 g of crude (S)-cyclohexyl 2-propenoyloxypropionate was obtained.

Workup

  1. additionwas added dropwise at a temperature of -20° C.
  2. customto separate an organic layer
  3. extractionan aqueous layer was extracted with methylene chloride
  4. washwashed with successive, saturated sodium bicarbonate solution, water, and saturated sodium chloride solution
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-78e5e1a0462341f9aa32412978b311ed
Source dataset
uspto-grants-1993_11
Patent number
US05266728

Reaction notes

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