Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 918

Reaction equation

HRID 918 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH:11]=[O:12].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C=O)C>[CH:18]1([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH:11]=[O:12])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8728Bromocyclopentane2×HCID 10796Cesium carbonate2×HCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Caesium carbonate (214 g, 0.66 mol) was added to a mixture of 3-hydroxy-4-methoxybenzaldehyde (100 g, 0.66 mol) and cyclopentyl bromide (98 g, 0.66 mol) in anhydrous DMF (50 ml). The reaction mixture was stirred at RT for 16 h then treated with a further portion of cyclopentyl bromide (98 g, 0.66 mol) and caesium carbonate (214 g, 0.66 mol). After a further 6 h at RT, the mixture was filtered and concentrated in vacuo. The residue was dissolved in dichloromethane (300 ml) and washed with sodium hydroxide solution (10%; 2×150 ml). The organic layer was dried (MgSO4), concentrated in vacuo, and distilled (150° C., 10-2 mbar) to afford the title compound (130 g) as a viscous colourless oil. (Found: C, 70.38; H, 7.48. C13H16O3 requires C, 70.89; H 7.32%); δH (CDCl3) 1.5-2.0 (8H, br m, CH2)4), 3.87 (3H, s, OMe), 4.80 (1H, br m, OCHCH2), 6.90 (1H, d, J 8.7 Hz. ArH ortho to OMe), 7.30-7.45 (2H, m. 2×ArH meta to OMe), and 9.77 (1 H, s, ArCHO).

Workup

  1. waitAfter a further 6 h at RT
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (300 ml)
  5. washwashed with sodium hydroxide solution (10%; 2×150 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. distillationdistilled (150° C., 10-2 mbar)

Sources & evidence

ORD record
ord-8d66976050a242adaad6949712ee0b51
Source dataset
uspto-grants-1998_03
Patent number
US05723460

Linked notes

Loading…