Potassium Hydroxide → HCID 53665626, compound

HRID 1383276Notes

Reaction equation

HRID 1383276 reaction equation
OC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([CH3:19])=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].[OH-].[K+].ClC(O)C(O)C.C[O-].[Na+]>CO>[CH3:19][C:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:18][O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 21187381HCID 21187381, compoundHCID 86757095HCID 86757095, compound

Product 1

HCID 53665626HCID 53665626, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

84.5 g (0.31 mol) of methyl 14-hydroxy-7-methyl-tetradec-6-enoate, 21 g of 86 percent potassium hydroxide in 220 ml of methanol, 72 g of chloropropane- 1,2-diol and 9 ml of 5.4M methanolic sodium methylate solution were mixed according to the procedure in Example 6. The product was distilled (b.p. 114° C.) in a high vacuum (0.1 Torr) and subsequently chromatographed. 29 g (38%) of 8-methyloxacyclopentadec-7-en-2-one were obtained having the following characteristics, Z/E=60/40;

Workup

  1. distillationThe product was distilled (b.p. 114° C.) in a high vacuum (0.1 Torr)
  2. customsubsequently chromatographed

Sources & evidence

ORD record
ord-ecf5f830df334630af95396f747cc351
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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