3,7,11,15-Tetramethylhexadec-2-en-1-ol → Oxacyclopentadecan-2-one

HRID 1167057Notes

Reaction equation

HRID 1167057 reaction equation
OCCCCCCCCCCCCC[C:15]([O:17][CH2:18][CH:19]=[C:20](C)[CH2:21][CH2:22][CH2:23][CH:24](C)[CH2:25][CH2:26][CH2:27][CH:28](C)[CH2:29][CH2:30]CC(C)C)=[O:16].CC(CCCC(C)CCCC(C)CCCC(C)C)=CCO.[O-2].[Mg+2]>>[CH2:24]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:15](=[O:16])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 1453863,7,11,15-Tetramethylhexadec-2-en-1-ol2×HCID 6850729Magnesium monoxideHCID 131724063HCID 131724063, compound

Product 1

HCID 77076Oxacyclopentadecan-2-oneYield 89%

Procedure

A 31.4 g (60.0 mmol) portion of 3,7,11,15-tetramethyl-2-hexadecenyl 14-hydroxytetradecanoate, 5.9 g (20 mmol) of 3,7,11,15-tetramethyl-2-hexadecenol and 0.5 g of magnesium oxide were put into the same apparatus of Inventive Example 1 and the reaction was carried out under conditions of 190 to 220° C. and 1.3 kPa to 130 Pa to obtain 33.5 g of a colorless and transparent distillate 6.5 hours thereafter. This distillate contained 12.1 g of cyclotetradecanolide (yield 89%) and 18.9 g of 3,7,11,15-tetramethyl-2-hexadecenol (recovery ratio 80%).

Workup

  1. customwas carried out under conditions of 190 to 220° C. and 1.3 kPa to 130 Pa
  2. customto obtain 33.5 g of a colorless and transparent distillate 6.5 hours

Sources & evidence

ORD record
ord-c188aacce511456f83912c8a075d7d37
Source dataset
uspto-grants-2003_09
Patent number
US06617304B1

Reaction notes

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