3-Chlorocyclopent-1-ene → 3-Cyclopent-2-enyloxy-4-methoxybenzaldehyde

HRID 993275Notes

Reaction equation

HRID 993275 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[H-].[Na+].Cl[CH:15]1[CH2:19][CH2:18][CH:17]=[CH:16]1>CN(C)C=O>[CH:19]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:18][CH2:17][CH:16]=[CH:15]1

Participants

5

Reactant 3

HCID 72973-Chlorocyclopent-1-eneHCID 12127IsovanillinHCID 24758Sodium hydride

Product 1

HCID 221458283-Cyclopent-2-enyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-hydroxy-4-methoxybenzaldehyde (14.20 g) in dry dimethylformamide (300 mL) is treated portionwise with sodium hydride (60% dispersion in oil; 3.70 g) at room temperature under nitrogen. 3-Chlorocyclo-pentene (9.6 mL) is added and the resulting mixture is stirred overnight. The solvent is then removed under reduced pressure and the residue is partitioned between water (500 mL) and dichloromethane (500 mL) and the aqueous layer is further extracted with dichloromethane (500 mL). The combined organic extracts are dried and evaporated under reduced pressure and the residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (1:1 v/v), to give 3-cyclopent-2-enyloxy-4-methoxybenzaldehyde, in the form of a pale brown oil (11.2 g).

Workup

  1. customThe solvent is then removed under reduced pressure
  2. customthe residue is partitioned between water (500 mL) and dichloromethane (500 mL)
  3. extractionthe aqueous layer is further extracted with dichloromethane (500 mL)
  4. customThe combined organic extracts are dried
  5. customevaporated under reduced pressure
  6. washeluting with a mixture of ethyl acetate and pentane (1:1 v/v)

Sources & evidence

ORD record
ord-ba5d6427e3534d949dab783b5f5cf3e3
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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