Hydrochloric Acid → (15-Acetoxy-pentadecanoyl)-cyclododecanone

HRID 1005612Notes

Reaction equation

HRID 1005612 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20])(=[O:3])[CH3:2].O1CCN([C:28]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=2)CC1.C(Cl)(Cl)Cl.Cl.[OH2:45]>>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH:39]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:28]1=[O:45])=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6212ChloroformHCID 77315HCID 77315, compoundHCID 1879209415-Acetoxy-pentadecanoyl chloride

Product 1

HCID 18792091(15-Acetoxy-pentadecanoyl)-cyclododecanone

Conditions

Temperature
46 °C

Procedure

15-Acetoxy-pentadecanoyl chloride (151 g; 0.47 mole) was added to a stirred mixture of 1-morpholino-cyclododecene (133 g; 0.53 mole) and chloroform (500 ml, free of alcohol) under nitrogen during 35 minutes. The temperature raised to 46° C. After stirring for 2 hours a mixture of 82 ml of water and 125 ml of hydrochloric acid (36%) was added and this mixture was refluxed for 4 hours at 62° C. After cooling the flask to room temperature the layers were separated and the organic ##STR7## layer was washed with 250 ml of iN hydrochloric acid. The water layer was extracted with 100 ml of chloroform. The combined chloroform layers were concentrated giving 240 g of crude (15-acetoxy-pentadecanoyl)-cyclododecanone.

Workup

  1. additionwas added
  2. temperaturethis mixture was refluxed for 4 hours at 62° C
  3. temperatureAfter cooling the flask to room temperature the layers
  4. customwere separated
  5. washthe organic ##STR7## layer was washed with 250 ml of iN hydrochloric acid
  6. extractionThe water layer was extracted with 100 ml of chloroform
  7. concentrationThe combined chloroform layers were concentrated

Sources & evidence

ORD record
ord-8d3f51cf5000486fb89ab88634b52dcf
Source dataset
uspto-grants-2000_04
Patent number
US06054599

Reaction notes

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