Bromocyclopentane → HCID 18319333, compound

HRID 1700866Notes

Reaction equation

HRID 1700866 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[OH:13][C:14]1[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[C:18]([CH:21]=1)[CH:19]=[O:20]>C(#N)C>[CH3:23][O:22][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:21][C:18]=1[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 3583415-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 18319333HCID 18319333, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

5.45 g of potassium carbonate (39.4 mmol) and 4.2 ml of bromocyclopentane (39.4 mmol) are added to a solution of 4 g of 5-hydroxy-2-methoxybenzaidehyde (26.3 mmol) in 27 ml of acetonitrile. The mixture is stirred for 16 hours at 80° C. and is then poured into ice-cold water and extracted with ether, and the organic phase is washed with normal aqueous sodium hydroxide solution and then with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate and filtered, and the solvent is evaporated off under vacuum. The title product is isolated by bulb-to-bulb oven distillation (T=200° C., P=10 mbar). 4.13 g of a pale yellow oil are obtained:

Workup

  1. additionis then poured into ice-cold water
  2. extractionextracted with ether
  3. washthe organic phase is washed with normal aqueous sodium hydroxide solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-13a57402b62d4e0485c18651e9e9d798
Source dataset
uspto-grants-2002_02
Patent number
US06350913B1

Reaction notes

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