Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 54591

Reaction equation

HRID 54591 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 carbonateHCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (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 (500 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 CS2CO3 (214 g, 0.66 mol). After a further 6h at RT, the mixture was filtered and concentrated in vacuo. The residue was dissolved in CH2Cl2 (300 ml) and washed with NaOH 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 colorless oil. δH (CDCl3) 1.5-2.0 (8H, br m, CH2)4), 3.87 (3H, s, OCH3), 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 (1H, s, ArCHO).

Workup

  1. filtrationAfter a further 6h at RT, the mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (300 ml)
  4. washwashed with NaOH solution (10%, 2×150 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. distillationdistilled (150° C., 10-2 mbar)

Sources & evidence

ORD record
ord-25e19a8ecbfe48e2aab63a4bb4fc0483
Source dataset
uspto-grants-1997_04
Patent number
US05622977

Linked notes

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