Ethanol → HCID 67249669, compound

HRID 1039974Notes

Reaction equation

HRID 1039974 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 (1N) 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 (1N)
  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-ebeb75b2295f4ee19852234803859c78
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

Loading…