Vanillin → HCID 59333851, compound

HRID 1616787Notes

Reaction equation

HRID 1616787 reaction equation
Br[CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4].[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>[CH3:13][O:12][C:11]1[CH:10]=[C:9]([CH:17]=[CH:16][C:14]=1[O:15][CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4])[CH:8]=[O:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 157383-Bromopentane

Product 1

HCID 59333851HCID 59333851, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Bromopentane (1.2 mL, 9.9 mmol) was added to a suspension of vanillin (1.0 g, 6.6 mmol), potassium carbonate (2.7 g, 20 mmol) in EtOH (10 mL) and treated according to Procedure 3. The crude product was purified by flash chromatography with 10% EtOAc/petrol as eluent to give 3-methoxy-4-(pent-3-yloxy)benzaldehyde (0.69 g, 47%) as a pale yellow oil; δH (400 MHz, CDCl3) 0.96 (t, J=7.2 Hz, 6H, CH3), 1.73 (m, 4H, CH2), 3.88 (s, 3H, OCH3), 4.23 (m, 1H, OCH), 6.94 (d, J5,6=8.0 Hz, 1H, H5), 7.40 (s, 1H, H2), 7.41 (d, J5,6=8.0 Hz, 1H, H6), 9.81 (s, 1H, CHO); δC (100 MHz, CDCl3) 9.6, 26.1, 56.0, 81.9, 109.8, 113.1, 126.5, 129.7, 150.5, 154.0, 190.7; vmax 1133, 1263, 1504, 1582, 1682, 2967 cm−1.

Workup

  1. additiontreated
  2. customThe crude product was purified by flash chromatography with 10% EtOAc/petrol as eluent

Sources & evidence

ORD record
ord-ca258520153d4c2b871905e4bb072f0f
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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