Cyclodecanone → Cyclododecanone

HRID 966460

Reaction equation

HRID 966460 reaction equation
[CH:1]([C:3]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2].C1(=O)CCCCCCCCC1>>[C:3]1(=[O:13])[CH2:1][CH2:2][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 73918CyclodecanoneHCID 134141611-Vinyl-1-cyclodecanol

Product 1

HCID 13246CyclododecanoneYield 52.8%

Procedure

0.5 g (2.7 mmol) of 1-vinyl-1-cyclodecanol (cf. I.1.3, comprises also about 8-10% cyclodecanone), quartz reactor 25/400 mm, temperature 670° C.±10, vaporization at 95-100° C. (airbath temperature) in about 10 min. Nitrogen stream about 2-2.5 l/h, vacuum 5-6 mbar. 0.45 g (90% crude yield) of a pure white condensate were obtained which partially crystallized into small fine needles. According to GC and GC/MS analyses, the mixture comprises, as main component, about 70% cyclododecanone, as well as 6-8% cyclodecanone and 2-3% starting material. Chromatographic separation of the mixture over silica gel (hexane/TBME 97:3) gave 0.26 g of cyclododecanone (52% isolated yield), which has identical retention times and spectroscopic properties as the commercially available compound (Fluka).

Workup

  1. custom400 mm, temperature 670° C.
  2. customat 95-100° C.
  3. customin about 10 min
  4. custom0.45 g (90% crude yield) of a pure white condensate were obtained which
  5. custompartially crystallized into small fine needles
  6. customChromatographic separation of the mixture over silica gel (hexane/TBME 97:3)

Sources & evidence

ORD record
ord-c89e9f6bfd4a49d3afcc9402ff527586
Source dataset
uspto-grants-2005_10
Patent number
US06951964B2

Linked notes

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