Cyclohexanone → HCID 10902204, compound

HRID 1523638Notes

Reaction equation

HRID 1523638 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-538dc8ec4bf745ffa7788e12802c96c5
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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