Ethanol → HCID 67249669, compound

HRID 410483Notes

Reaction equation

HRID 410483 reaction equation
S(=O)(=O)(O)O.[O:6]=[C:7]1[CH2:12][CH2:11][C@@H:10]([C:13]([OH:15])=[O:14])[C@H:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8]1.[CH3:22][CH2:23]O>>[O:6]=[C:7]1[CH2:12][CH2:11][C@@H:10]([C:13]([O:15][CH2:22][CH3:23])=[O:14])[C@H:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:8]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 67433022HCID 67433022, compound

Product 1

HCID 67249669HCID 67249669, compoundYield 31%

Procedure

Sulfuric acid (0.073 ml, 1.375 mmol) was added to a mixture of (trans)-4-oxo-2-phenylcyclohexanecarboxylic acid (1.5 g, 6.87 mmol) in EtOH (15 ml). The reaction was aged at 77° C. for 14 h. The cooled reaction was quenched with NaOH (1/V) and extracted three times with CH2Cl2. The combined organic layers were dried under reduced pressure and purified via silica gel column chromatography (0-40% EtOAc:Hexanes) to afford ethyl(trans)-4-oxo-2-phenylcyclohexanecarboxylate (526 mg, 31%) as a colorless oil. MS ESI: [M+H]+ m/z 247.

Workup

  1. customThe cooled reaction
  2. customwas quenched with NaOH (1/V)
  3. extractionextracted three times with CH2Cl2
  4. customThe combined organic layers were dried under reduced pressure
  5. custompurified via silica gel column chromatography (0-40% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-ad3b2126b9104889aaf328084dc8e636
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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