Water → HCID 178515944, compound

HRID 322790

Reaction equation

HRID 322790 reaction equation
C([C:5]1[CH:12]=[C:11](C(C)(C)C)[CH:10]=[C:7]([CH:8]=O)[C:6]=1[OH:17])(C)(C)C.[C:18]([C:22]1[CH:27]=[C:26](C(C)(C)C)[CH:25]=[CH:24][C:23]=1[OH:32])(C)(C)C.[NH2:33][C@H:34]1CCCC[C@@H:35]1[NH2:40].O>C(O)C>[CH:11]1[CH:12]=[CH:5][C:6](=[O:17])/[C:7](=[CH:8]\[NH:33][CH2:34][CH2:35][NH:40]/[CH:18]=[C:22]2\[C:23]([CH:24]=[CH:25][CH:26]=[CH:27]\2)=[O:32])/[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73112,4-Di-tert-butylphenolHCID 4793071,2-Diaminocyclohexane, (+)-HCID 6880233,5-Di-tert-butylsalicylaldehyde

Product 1

HCID 178515944HCID 178515944, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Di-t-butylsalicylaldehyde (2.0 equivalents) (prepared from the inexpensive, commercially available 2,4-di-t-butylphenol according to Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org Chem 1994, 59, 1939) was added as a solid to a 0.2 M solution of (S,S)-1,2-diaminocyclohexane (1.0 equivalent) (Aldrich Chemical Co., Milwaukee, Wis.) in absolute ethanol. The mixture was heated to reflux for 1 hr. and then H2O was added dropwise to the cooled bright yellow solution. The resulting yellow crystalline solid was collected by filtration and washed with a small portion of 95% ethanol. The yield of analytically pure salen ligand obtained in this manner was 90-97%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hr
  3. filtrationThe resulting yellow crystalline solid was collected by filtration
  4. washwashed with a small portion of 95% ethanol

Sources & evidence

ORD record
ord-5cbfd22f7bf54879a0b0d103e4513491
Source dataset
uspto-grants-2001_04
Patent number
US06211370B1

Linked notes

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