Cyclododecanemethanol → Cyclododecanecarboxaldehyde

HRID 129526

Reaction equation

HRID 129526 reaction equation
[CH:1]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1(C)N([O])C(C)(C)CCC1.[Br-].[Na+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH:1]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 74686CyclododecanemethanolHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium Hypochlorite

Product 1

HCID 78737CyclododecanecarboxaldehydeYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9.92 g (50 mmol) of cyclododecane methanol in 100 ml of methylene chloride under a nitrogen atmosphere is added 50 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (TEMPO) and 510 mg (5 mmol) of sodium bromide in 5 ml of water. The solution is cooled to 10°-15° C. and a solution of 100 ml of 5.25% aqueous sodium hypochlorite and 2.0 g of sodium bicarbonate is added over 1 hour. The reaction mixture is allowed to warm to room temperature and after 1 hour is diluted with methylene chloride. The organic phase is washed with aqueous sodium thiosulfate, aqueous bicarbonate and water. The methylene chloride layer is dried over magnesium sulfate, filtered and evaporated in vacuo to give 9.43 g of crude title compound as an oil: IR (film) 1723 cm-1 ; NMR (CDCl3)) δ 1.34 (bs, 18 H), 1.41 (m, 4 H), 1.54 (m, 2 H), 1.65 (m, 2 H), 2.40 (m, 1 H), 9.64 (d, 1 H, J=1.6 Hz) M+ (EI) 196

Workup

  1. temperatureThe solution is cooled to 10°-15° C.
  2. washThe organic phase is washed with aqueous sodium thiosulfate, aqueous bicarbonate and water
  3. dry with materialThe methylene chloride layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-5e4a7d55dcea4bc38d8a7c230fd2475e
Source dataset
uspto-grants-1995_11
Patent number
US05468774

Linked notes

Loading…