Methyl 15-Hydroxypentadecanoate → Pentadecalactone

HRID 1167059Notes

Reaction equation

HRID 1167059 reaction equation
OC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[O-2].[Mg+2]>>[CH2:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[O:18][CH2:19][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 3

HCID 3496889Methyl 15-HydroxypentadecanoateHCID 6850729Magnesium monoxideHCID 178419056HCID 178419056, compound

Product 1

HCID 235414PentadecalactoneYield 95%

Procedure

A 13.1 g (48.1 mmol) portion of methyl 15-hydroxypentadecanoate, 45.1 g (100 mmol) of polyoxyethylene lauryl ether {average addition mol number 6} and 1.0 g of magnesium oxide were put into the same apparatus of Inventive Example 1, and the reaction was carried out under ambient pressure to 1.3 kPa and at 190 to 245° C. for 3 hours, while distilling out methanol, and then under 53 Pa and at 160 to 260° C. to obtain 19.5 g of a colorless to light yellow liquid. This distillate contained 11.0 g of cyclopentadecanolide (yield 95%).

Workup

  1. distillationwhile distilling out methanol
  2. customunder 53 Pa and at 160 to 260° C. to obtain 19.5 g of a colorless to light yellow liquid

Sources & evidence

ORD record
ord-4752cdfa952e40079ab72f7202f5bfb8
Source dataset
uspto-grants-2003_09
Patent number
US06617304B1

Reaction notes

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