Potassium Hydroxide → HCID 53743879, compound

HRID 1383273Notes

Reaction equation

HRID 1383273 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH3:18])=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].[OH-].[K+]>OCC(CO)O>[CH3:18][C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 131722725HCID 131722725, compound

Product 1

HCID 53743879HCID 53743879, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
152 °C

Procedure

24.5 g (95.5 mol) of 14-hydroxy-9-methyltetradec-8-enoic acid, (Z/E=80/20) were placed in 50 ml of glycerol and treated with 0.54 g of potassium hydroxide (50 percent). The resulting water was distilled off. Thereupon, the distillation headpiece was removed and the special headpiece (see FIG. 1) was fitted and filled with glycerol. After the addition of 1 g of sodium methylate the mixture was heated to 152° C., 6 mbar. After 24 hours the addition of 1 g of MeONa was again effected. After 48 hours extraction of the content of the special headpiece yielded 19 g of crude product. By chromatography 19 g (82%) of 10-methyloxacyclopentadec-9-en-2-one were obtained having the following characteristics: Z/E=80/20;

Workup

  1. distillationThe resulting water was distilled off
  2. customThereupon, the distillation headpiece was removed
  3. customthe special headpiece (see FIG. 1) was fitted
  4. additionfilled with glycerol
  5. additionAfter the addition of 1 g of sodium methylate the mixture
  6. additionAfter 24 hours the addition of 1 g of MeONa
  7. extractionAfter 48 hours extraction of the content of the special headpiece
  8. customyielded 19 g of crude product

Sources & evidence

ORD record
ord-07381583295449139c2d9586edd195e5
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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