Cyclododecanemethanol → Cyclododecanecarboxaldehyde

HRID 2380357Notes

Reaction equation

HRID 2380357 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 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)) δ1.34 (bs, 18 H), 1.41 (m, 4H), 1.54 (m, 2H), 1.65 (m, 2H), 2.40 (m, 1H), 9.64 (d, 1H, J=1.6 Hz) M+ (El) 196

Workup

  1. temperatureThe solution is cooled to 10°-15° C.
  2. washThe organic phase is washed with aqueous sodium 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-0a22fe979f0947a999351ba0e7d42624
Source dataset
uspto-grants-1994_11
Patent number
US05366993

Reaction notes

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