Cyclohexanone → HCID 10902204, compound

HRID 534081Notes

Reaction equation

HRID 534081 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 mH 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 mH Hg
  5. customthe 125-140° C. fraction was collected

Sources & evidence

ORD record
ord-9db63db93f9544ed8b35baf334f384ee
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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