Decyltetradecanol → Pentadecalactone

HRID 1167058Notes

Reaction equation

[CH2:1]([OH:17])[CH2:2][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][OH:16].C(C(CCCCCCCCCCCC)CO)CCCCCCCCC>>[CH2:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

Reactant 2

HCID 93875Decyltetradecanol

HCID 5189941,15-Pentadecanediol

Product 1

HCID 235414PentadecalactoneYield 240.5%

Procedure

A 54 g portion of the hydrogenated product obtained in Reference Example 2 and 0.2 g of magnesium oxide were put into the same apparatus of Inventive Example 1 and the reaction was carried out under conditions of 230 to 260° C. and 1.3 kPa to 130 Pa to obtain 15.2 g of a colorless liquid distillate 3 hours thereafter. This distillate contained 2.2 g of cyclopentadecanolide (yield 94%), 0.93 g of 1,15-pentadecanediol (recovery ratio 96%) and 11.3 g of 2-decyl-1-tetradecanol. The reaction residue was a light yellow liquid having a viscosity of 85 mPa·s, and 28.4 g of di-2-decyl-1-tetradecyl pentadecandioate was recovered from the residue (recovery ratio 85%).

Sources & evidence

ORD record: ord-6e08d86a544d4eca84f606ea63371f18
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617304B1

Reaction notes

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