Ethanol → HCID 178472374, compound

HRID 1893333Notes

Reaction equation

HRID 1893333 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:10][C:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([CH2:2][OH:1])[CH2:8][CH2:7]1)=[O:11])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 178525728HCID 178525728, compound

Product 1

HCID 178472374HCID 178472374, compoundYield 98.1%

Procedure

To a solution of cis/trans-4-(hydroxymethyl)cyclohexanecarboxylic acid (10.0 g, 63.2 mmol) in ethanol (316 ml) was added a catalytic amount of sulfuric acid. The reaction mixture was heated at reflux for 20 h. The solvent was evaporated. The residue was partitioned between ethyl acetate (150 ml) and 2 M aqueous sodium carbonate solution (100 ml). The aqueous layer was separated. The organic layer was washed with one 100-ml portion of water and one 50-ml portion of brine. The combined aqueous layers were extracted with one 100-ml portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the tile compound as colorless oil (11.5 g, 98.1%). MS m/e: 187 ([M+H]+)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customThe solvent was evaporated
  4. customThe residue was partitioned between ethyl acetate (150 ml) and 2 M aqueous sodium carbonate solution (100 ml)
  5. customThe aqueous layer was separated
  6. washThe organic layer was washed with one 100-ml portion of water and one 50-ml portion of brine
  7. extractionThe combined aqueous layers were extracted with one 100-ml portion of ethyl acetate
  8. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6f6bd02ef904ecbb9d850b19ea35483
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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