3-Chloro-1,2-propanediol → HCID 70190292, compound

HRID 1383271Notes

Reaction equation

HRID 1383271 reaction equation
OC[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[OH-].[K+].ClCC(O)CO>CO>[O:19]1[CH2:20][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1=[O:18]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 14797Potassium HydroxideHCID 53309397HCID 53309397, compound

Product 1

HCID 70190292HCID 70190292, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

240 g (0.84 mol) of methyl Z-16-hydroxyhexadec-11-enoate and 50 g of potassium hydroxide were dissolved in 500 ml of methanol in a 3 liter flask. The mixture was heated to reflux temperature for 2 hours. Then, the methanol was distilled off and 800 ml of glycerol were added to the residue. 250 ml of glycerol were distilled off (150° C., 3 mmHg). 160 g (1.45 mol) of 3-chloropropane-1,2-diol were added slowly at 150° C. and the mixture was stirred at this temperature for 1 hour. Then, 200 ml of a mixture of 3-chloropropane-1,2-diol and glycerol were distilled off (120-148° C. 3 mmHg, internal temperature 160-170° C.). The mixture was cooled to 60° C. and treated at this temperature with 25 ml of 5.4M ethanolic sodium methanolate solution. The mixture was distilled further (3 mmHg, 180-200° C.) and glycerol was replaced continuously. After 950 ml of a two-phase mixture had been distilled off the residue was extracted with hexane. After distillation there were obtained 167 g (78%) of 12Z-oxacycloheptadec-12-en-2-one, were obtained having the following characteristics: Z/E=91/9;

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature for 2 hours
  3. distillationThen, the methanol was distilled off
  4. addition800 ml of glycerol were added to the residue
  5. distillation250 ml of glycerol were distilled off (150° C., 3 mmHg)
  6. distillationThen, 200 ml of a mixture of 3-chloropropane-1,2-diol and glycerol were distilled off (120-148° C. 3 mmHg, internal temperature 160-170° C.)
  7. additiontreated at this temperature with 25 ml of 5.4M ethanolic sodium methanolate solution
  8. distillationThe mixture was distilled further (3 mmHg, 180-200° C.) and glycerol
  9. distillationAfter 950 ml of a two-phase mixture had been distilled off the residue
  10. extractionwas extracted with hexane
  11. distillationAfter distillation

Sources & evidence

ORD record
ord-8621cfd96f6048d89d947d3a8dd4f41b
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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