Phenol → 2-Phenoxy-1-formyl-1-cyclopentene

HRID 1042969Notes

Reaction equation

HRID 1042969 reaction equation
Cl[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[CH:7]=[O:8].[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[O:15]([C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[CH:7]=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 123899702-Chlorocyclopent-1-ene-1-carbaldehyde

Product 1

HCID 534956442-Phenoxy-1-formyl-1-cyclopentene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of residue (100 g, 0.77 mol) obtained in example 1 in acetone (400 mL), phenol (79.3 g, 0.84 mol) and K2CO3 (126.8 g, 0.92 mol) were added. The mixture was stirred under nitrogen for 12 hours at room temperature and monitored by TLC (petroleum ether/ethyl acetate=10:1). After the reaction completed, the solvent was removed on a rotary evaporator, and water (300 mL) was added. The mixture was extracted with EtOAc (2×100 mL). The organic layer was washed with aqueous sodium carbonate (2×50 mL) and water (50 mL). After dried over sodium sulfate, the solvent was removed and 2-phenoxy-1-formyl-1-cyclopentene was obtained (155 g, contains some phenol), which was used directly in the next step.

Workup

  1. customthe solvent was removed on a rotary evaporator, and water (300 mL)
  2. additionwas added
  3. extractionThe mixture was extracted with EtOAc (2×100 mL)
  4. washThe organic layer was washed with aqueous sodium carbonate (2×50 mL) and water (50 mL)
  5. dry with materialAfter dried over sodium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-8da65ae1cad84198b4a484f198fb4ff0
Source dataset
uspto-grants-2013_10
Patent number
US08558023B2

Reaction notes

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