Oxalyl chloride → HCID 178445653, compound

HRID 1791192Notes

Reaction equation

HRID 1791192 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C=O)C>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([Cl:17])=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 178445658HCID 178445658, compound

Product 1

HCID 178445653HCID 178445653, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

11.0 g (59.7 mmol) trans-4-tert-Butylcyclohexanecarboxylic acid are dissolved in 400 ml dichloromethane plus a few drops of DMF, 9.09 g (71.6 mmol) ethanedioyl dichloride are added and the solution is stirred at room temperature for one hour. The mixture is then stirred at reflux for two hours and, after cooling down to room temperature, evaporated to dryness in vacuo. The residue is then dissolved in toluene two times and again evaporated to dryness in vacuo. The residue is used in the next step without further purification.

Workup

  1. stirringThe mixture is then stirred
  2. temperatureat reflux for two hours
  3. temperatureafter cooling down to room temperature
  4. customevaporated to dryness in vacuo
  5. dissolutionThe residue is then dissolved in toluene two times
  6. customagain evaporated to dryness in vacuo
  7. customThe residue is used in the next step without further purification

Sources & evidence

ORD record
ord-57330aed75694e0fb1c2e0f3489fd77b
Source dataset
uspto-grants-2006_07
Patent number
US07074790B2

Reaction notes

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