Cyclohexanone → HCID 10902204, compound

HRID 1511101Notes

Reaction equation

HRID 1511101 reaction equation
[OH:1][C@H:2]([C@@H:8]([OH:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:15]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C1(C)C=CC=CC=1>[O:1]1[C:15]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:14][C@@H:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@@H:2]1[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 6993580Diethyl tartrate

Product 1

HCID 10902204HCID 10902204, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2R,3R)-diethyl 2,3-dihydroxysuccinate (82.99 ml, 485.0 mmol) was dissolved in Toluene (400 mL) and cyclohexanone (55.29 ml, 533.5 mmol) and Amberlyst 15 ion-exchange resin (2.0 g) were added and the reaction refluxed under dean stark trap for 12 hours. The reaction was cooled to ambient temperature, filtered and concentrated. The residue was distilled at 0.5 mM Hg and the 125-140° C. fraction was collected to afford (2R,3R)-diethyl 1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate (91.3 g, 66% yield).

Workup

  1. temperaturethe reaction refluxed under dean stark trap for 12 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. distillationThe residue was distilled at 0.5 mM Hg
  5. customthe 125-140° C. fraction was collected

Sources & evidence

ORD record
ord-994c88f35d004d4090a6e8bb330b07c4
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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