Hydrochloric Acid → 3-Furancarboxylic acid, 5-cyclohexyl-2-methyl-

HRID 2236186Notes

Reaction equation

HRID 2236186 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:8][C:7]=1[CH3:17])=[O:5])C.[OH-].[Na+].Cl>C(O)C.O>[CH:11]1([C:9]2[O:8][C:7]([CH3:17])=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 675376085-Cyclohexyl-2-methyl-furan-3-carboxylic acid ethyl ester

Product 1

HCID 593014193-Furancarboxylic acid, 5-cyclohexyl-2-methyl-Yield 76.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-cyclohexyl-2-methyl-furan-3-carboxylic acid ethyl ester (143 mg, 0.605 mmol) and 2N sodium hydroxide (1.5 mL, 3.0 mmol) in 3 mL ethanol and 1.5 mL water was heated to reflux for 1 hour. The reaction mixture was cooled, pH adjusted to 1 with 1N HCl and extracted with CH2Cl2 (5×40 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give 5-cyclohexyl-2-methyl-furan-3-carboxylic acid (96 mg, 76%).

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with CH2Cl2 (5×40 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-44f4b43e9cad4c82baae5afee06a3c0c
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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