Oxygen → Tridecanoic acid

HRID 597280

Reaction equation

HRID 597280 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]CC.CN(C)[CH:17]=[O:18].[N+]([O-])([N+]([O-])=O)=[O:21].O=O.[O-2].[Ca+2]>C1C=CC=CC=1>[C:17]([OH:18])(=[O:21])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 5

HCID 977Oxygen2×HCID 6228DimethylformamideHCID 142601-TetradeceneHCID 25352Nitrogen oxide (N2O4)HCID 6850728Calciumoxide

Product 1

HCID 12530Tridecanoic acidYield 92.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetradecene (19.8 grams, 0.1 mole) and dimethylformamide (20 milliliters, 0.26 mole) dissolved in 100 milliliters of benzene were treated with a 1:6 volume to volume ratio mixture of dinitrogen tetroxide (9.2 grams, 0.1 mole) and oxygen at 10° C. over a period of four hours and the mixture was swept with oxygen for an additional 15 minutes. Calcium oxide (5.6 grams, 0.1 mole) was added to the cooled stirred mixture and after 30 minutes, the solid material (37.6 grams) was separated by filtration and 300 milliliters of water were added thereto. After one hour at reflux, the solution was cooled and acidified with 6N hydrochloric acid to precipitate 19.8 grams (92 percent yield) of tridecanoic acid.

Workup

  1. customthe solid material (37.6 grams) was separated by filtration and 300 milliliters of water
  2. additionwere added
  3. temperatureAfter one hour at reflux
  4. temperaturethe solution was cooled

Sources & evidence

ORD record
ord-5ad06f5b9feb446a87ee6c447d58e99d
Source dataset
uspto-grants-1977_03
Patent number
US04013697

Linked notes

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