Vanillin → 4-Cyclopentyloxy-3-methoxy-benzaldehyde

HRID 1616754Notes

Reaction equation

HRID 1616754 reaction equation
Br[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[O:7]=[CH:8][C:9]1[CH:17]=[CH:16][C:14]([OH:15])=[C:11]([O:12][CH3:13])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH:2]1([O:15][C:14]2[CH:16]=[CH:17][C:9]([CH:8]=[O:7])=[CH:10][C:11]=2[O:12][CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1183VanillinHCID 8728BromocyclopentaneHCID 11430Potassium Carbonate

Product 1

HCID 31527214-Cyclopentyloxy-3-methoxy-benzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromocyclopentane (7.0 mL, 66 mmol) was added to a suspension of vanillin (5.0 g, 33 mmol) and potassium carbonate (13.6 g, 99 mmol) in EtOH (75 mL) and treated according to Procedure 3. 4-Cyclopentyloxy-3-methoxybenzaldehyde (7.1 g, 98%) was obtained as a yellow oil; δH (400 MHz, CDCl3) 1.62 (m, 2H, CH2), 1.78-2.04 (m, 6H, CH2), 3.89 (s, 3H, OCH3), 4.86 (tt, J=6.0, 3.2 Hz, 1H, OCH), 6.94 (d, J5,6=8.0 Hz, 1H, H5), 7.38 (d, J2,6=2.0 Hz, 1H, H2), 7.41 (dd, J5,6=8.0, J2,6=2.0 Hz, 1H, H6), 9.82 (s, 1H, CHO); δC (100 MHz, CDCl3) 24.1, 32.8, 56.0, 80.6, 109.4, 112.8, 126.6, 129.5, 150.2, 153.4, 190.9; vmax 977, 1260, 1504, 1580, 1680, 2869, 2956 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-ff8e0295948343b5a9e9c1e7b61146c6
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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