Cyclododecanone → Cyclotetradecan-1-one

HRID 966459Notes

Reaction equation

HRID 966459 reaction equation
[CH:1]([C:3]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2].C1(=O)CCCCCCCCCCC1>>[C:3]1(=[O:15])[CH2:1][CH2:2][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 13246CyclododecanoneHCID 543425HCID 543425, compound

Product 1

HCID 77153Cyclotetradecan-1-oneYield 72%

Procedure

5 g (23.8 mmol) of 1-vinylcyclododecanol, quartz reactor 25/400 mm, temperature 660° C.±10, vaporization at 125-135° C. (airbath temperature) in about 30 min. Nitrogen stream about 1-2 l/h, vacuum 4-6 mbar. The oily condensate began to crystallize in the cool trap already. 4.4 g (88% crude yield) of a wax-like solid were obtained which, according to GC and GC/MS analyses, comprises as well as 80-85% of the main component also up to about 5% cyclododecanone and about 5-10% other components which, according to the molecular masses found, are dehydrogenation products. Recrystallization twice from hexane at 0° and −20° C., gave 3.6 g (72%) of cyclotetradecanone (GC purity>98%) as colorless needles with a melting point of 56° C.

Workup

  1. customto crystallize in the cool trap already
  2. custom4.4 g (88% crude yield) of a wax-like solid were obtained which
  3. customRecrystallization twice from hexane at 0°

Sources & evidence

ORD record
ord-2619c7353c0f44839900ed27e14c07ff
Source dataset
uspto-grants-2005_10
Patent number
US06951964B2

Reaction notes

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