Formaldehyde → HCID 12536974, compound

HRID 2205244Notes

Reaction equation

HRID 2205244 reaction equation
[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:14](=O)([O-])[O-:15].[K+].[K+].C=O>C(#N)C.O>[OH:15][CH2:14][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:1]1=[O:13]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 13246Cyclododecanone

Product 1

HCID 12536974HCID 12536974, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of cyclododecanone (1) (5.0 g, 27.47 mmol, 1 equiv) and potassium carbonate (0.06 g, 0.41 mmol, 0.015 equiv) in acetonitrile (20 mL) and water (2 mL) was added formaldehyde (37% in water) (4.2 mL, 52.20 mmol, 1.9 equiv) at 40° C. dropwise. The reaction was stirred at 40° C. for 4 hours, then cooled to room temperature and extracted with diethyl ether (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, concentrated under reduced pressure. The crude product was purified on an AnaLogix system using a gradient of 0 to 30% ethyl acetate in heptanes to give the desired product as a clear oil, which slowly solidifies to a white solid (2.5 g, 43% yield).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with diethyl ether (3×50 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified on an AnaLogix system

Sources & evidence

ORD record
ord-84bddfbecd1c490b93e38f5528a34c7d
Source dataset
uspto-grants-2016_06
Patent number
US09371265B2

Reaction notes

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