Ethanol → 1,4,7-Trioxa-10-azacyclododecane

HRID 542925Notes

Reaction equation

HRID 542925 reaction equation
C([N:8]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)C>[Pd].[H][H]>[NH:8]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 702EthanolHCID 766194HCID 766194, compound2×

Product 1

HCID 5458171,4,7-Trioxa-10-azacyclododecaneYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A quantity of the 1-benzyl-1-aza-4,7,10-trioxacyclododecane compound (3) prepared in Example 3 (45.1 g, 0.17 mol), ethanol (7 g), and 10% palladium on carbon (0.5 g) were shaken in hydrogen atmosphere at more than 50 psi (1 psi=6.9×103 Pa=0.07 kg cm-2). Hydrogen gas was recharged several times into the reaction chamber to keep the pressure elevated. Shaking was continued until the pressure lowering stopped (4 days). After the palladium carbon was filtered, the solvent was evaporated. The pure compound (4) was sublimed from the residue with gentle heating using a water bath (75°-77° C.; crude material melted at this temperature). The sublimate was white needles and was hygroscopic. Yield 60%; 1HNMR (D2O): δ 2.53-2.70 (t, 4H, N--CH2), 3.5-3.75 (m, 12H, O--CH2), no signal at 7.1 (Ar--H of benzyl group, possible contaminant).

Workup

  1. custom(4 days)
  2. filtrationAfter the palladium carbon was filtered
  3. customthe solvent was evaporated
  4. temperaturewith gentle heating
  5. custom75°-77° C.

Sources & evidence

ORD record
ord-c144739aa771408ea19121905fabf80c
Source dataset
uspto-grants-1987_04
Patent number
US04659815

Reaction notes

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