Formic Acid → 1-Methylcyclopentane-1-carboxylic acid

HRID 1737275Notes

Reaction equation

HRID 1737275 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:7]([OH:9])=[O:8]>S(=O)(=O)(O)O>[CH3:1][C:6]1([C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 8079Cyclohexene

Product 1

HCID 1384361-Methylcyclopentane-1-carboxylic acidYield 2.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Cyclohexene (25 ml, 0.246 mol) was treated with conc. sulphuric acid (100 ml) and formic acid (18.9 ml, 0.5 mol) at 5° C. for two hours. The mixture was poured onto ice and extracted twice with EtOAc. The organic extracts were washed with brine, then extracted with 2M KOH. The basic extract was acidified with 2M HCl and extracted with CHCl3, filtered (Whatman® 1 PS phase separator) and evaporated. The resultant brown oil was purified by bulb-to-bulb distillation (125° C./oil pump) to give the title compound as a colourless oil (860 mg, 2%).

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted twice with EtOAc
  3. washThe organic extracts were washed with brine
  4. extractionextracted with 2M KOH
  5. extractionThe basic extract
  6. extractionextracted with CHCl3
  7. filtrationfiltered (Whatman® 1 PS phase separator)
  8. customevaporated
  9. distillationThe resultant brown oil was purified by bulb-to-bulb distillation (125° C./oil pump)

Sources & evidence

ORD record
ord-ebdbb4b5fb8440b5a5b8119b34b1918e
Source dataset
uspto-grants-1999_10
Patent number
US05962451

Reaction notes

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