Methanol → HCID 53826314, compound

HRID 434417Notes

Reaction equation

HRID 434417 reaction equation
[CH3:1][C:2]1[CH2:13][CH2:12][C:11]([CH3:14])=[CH:10][CH2:9][CH2:8][C:7]([CH3:15])=[CH:6][CH2:5][CH2:4][CH:3]=1.[CH3:16][OH:17]>>[CH3:16][O:17][C:2]1([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:14])[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 887MethanolHCID 894321,5,9-Cyclododecatriene, 1,5,10-trimethyl-

Product 1

HCID 53826314HCID 53826314, compoundYield 95%

Procedure

340 g (1.67 M) of 2,5,9-trimethyl-cyclododeca-1,5,9-triene and 110 g of acidic diatomaceous earth in 5000 ml of methanol (containing less than 0.05% of water) were refluxed during 40 h. After cooling at room temperature and filtration, the mixture was concentrated at reduced pressure to yield, after a distillation, 366 g of a product having b.p. 79°-110°/0.01 Torr. After fractional distillation, 212 g of starting 2,5,9-trimethylcyclododeca-1,5,9-triene (b.p.43°-52°/0.1 Torr) and 140 g of the desired product, b.p. 78°-82°/0.01 Torr (yield 95% based on the converted starting material).

Workup

  1. filtrationfiltration
  2. concentrationthe mixture was concentrated at reduced pressure
  3. customto yield
  4. distillationafter a distillation, 366 g of a product
  5. distillationAfter fractional distillation, 212 g of starting 2,5,9-trimethylcyclododeca-1,5,9-triene (b.p.43°-52°/0.1 Torr) and 140 g of the desired product, b.p. 78°-82°/0.01 Torr (yield 95%

Sources & evidence

ORD record
ord-d7cd18bdf6aa497c8dfb219e9860e638
Source dataset
uspto-grants-1983_08
Patent number
US04396781

Reaction notes

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