Boron trifluoride etherate → Cyclododecanecarboxaldehyde

HRID 37304

Reaction equation

HRID 37304 reaction equation
[O:1]1[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1.B(F)(F)F.CCOCC.CCCCCC.CCCCCC.C(OCC)(=O)C>CCOCC>[CH:3]1([CH:2]=[O:1])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8058HexaneHCID 110198001-Oxaspiro[2.11]tetradecaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 78737CyclododecanecarboxaldehydeYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 5.0 g (25.5 mmol) of 1-oxaspiro[2.11]tetradecane in 50 ml of dry ether at 0° C. is slowly added 1.8 ml (2.1 g, 14.6 mmol) of boron trifluoride etherate. The ice bath is removed and after 15 minutes at room temperature the solution is partitioned between ether and saturated sodium bicarbonate. The organic phase is evaporated to give a clear oil. Flash chromatography over silica gel using a hexane to hexane:ethyl acetate (9:1) gradient give 1.6 g (34%) of a clear oil: NMR (CDCl3) δ 1.28-1.8 (m, 18H), 2.03 (s, 1H), 2.42 (m, 1H), 9.62 (s, 1H)

Workup

  1. customat 0° C.
  2. customThe ice bath is removed and after 15 minutes at room temperature the solution
  3. customis partitioned between ether and saturated sodium bicarbonate
  4. customThe organic phase is evaporated
  5. customto give a clear oil

Sources & evidence

ORD record
ord-2af3065affd844bd99ccf33cda805453
Source dataset
uspto-grants-1995_05
Patent number
US05420153

Linked notes

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