Formamide → Ethyl alpha-(p-phenoxyphenoxy)alpha-cyclohexylacetate

HRID 1277634Notes

Reaction equation

HRID 1277634 reaction equation
[Na].[O:2]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH:17]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(N)=O>C(O)C>[O:2]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:17]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 713FormamideHCID 132544-PhenoxyphenolHCID 2762757Ethyl 2-bromo-2-cyclohexylacetateHCID 5360545Sodium

Product 1

HCID 13020962Ethyl alpha-(p-phenoxyphenoxy)alpha-cyclohexylacetateYield 44.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into 15 ml of anhydrous ethanol, 205 mg (0.0089 mole) of methallic sodium was dissolved and then, 1.8 g (0.0089 mole) of p-phenoxyphenol was added. The mixture was stirred at room temperature for about 30 minutes. Ethanol was distilled off under a reduced pressure and 5 ml of dimethyl formamide was added to the residue and dimethyl formamide was distilled off under a reduced pressure and then, 15 ml of dimethyl formamide was added to the residue to dissolve it. Into the solution, 2.5 g (0.010 mole) of ethyl α-bromo-α-cyclohexylacetate was added. The mixture was refluxed for 8 hours and then diemethyl formamide was distilled off under a reduced pressure. The residue was admixed with 50 ml of water and extracted twice with 50 ml of benzene. The benzene layers were combined and washed three times with 30 ml of 5% NaOH aq.sol. and then with water and dehydrated over sodium sulfate and distilled in vacuum to obtain 1.4 g of ethyl α-(p-phenoxyphenoxy)α-cyclohexylacetate (yield: 42.6%).

Workup

  1. distillationEthanol was distilled off under a reduced pressure and 5 ml of dimethyl formamide
  2. additionwas added to the residue and dimethyl formamide
  3. distillationwas distilled off under a reduced pressure
  4. addition15 ml of dimethyl formamide was added to the residue
  5. dissolutionto dissolve it
  6. temperatureThe mixture was refluxed for 8 hours
  7. distillationwas distilled off under a reduced pressure
  8. extractionextracted twice with 50 ml of benzene
  9. washwashed three times with 30 ml of 5% NaOH aq.sol
  10. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-bad90d2ee41f474eb5c9a0e5ba89d250
Source dataset
uspto-grants-1981_07
Patent number
US04278678

Reaction notes

Loading…