Vanillin → HCID 22022329, compound

HRID 1616756Notes

Reaction equation

HRID 1616756 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[O:8]=[CH:9][C:10]1[CH:18]=[CH:17][C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CCO>[CH:2]1([O:16][C:15]2[CH:17]=[CH:18][C:10]([CH:9]=[O:8])=[CH:11][C:12]=2[O:13][CH3:14])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 1183VanillinHCID 5238Sodium IodideHCID 7960Cyclohexyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 22022329HCID 22022329, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromocyclohexane (8.0 mL, 66 mmol) was added to a suspension of vanillin (5.0 g, 33 mmol), potassium carbonate (13.6 g, 99 mmol) and sodium iodide (0.49 g, 3.3 mmol) in EtOH (75 mL) and treated according to Procedure 3 for 64 h. The crude product was purified by flash chromatography with 10-15% EtOAc/petrol as eluent to give 4-cyclohexyloxy-3-methoxybenzaldehyde (2.8 g, 37%) as a pale yellow oil; δH (400 MHz, CDCl3) 1.27-1.43 (m, 4H, CH2), 1.56 (m, 2H, CH2), 1.85 (m, 2H, CH2), 2.06 (m, 2H, CH2), 3.91 (s, 3H, OCH3), 4.37 (tt, J=9.4, 3.6 Hz, 1H, OCH), 6.98 (d, J5,6=8.0 Hz, 1H, H5), 7.40 (d, J2,6=2.0 Hz, 1H, H2), 7.42 (dd, J5,6=8.0, J2,6=2.0 Hz, 1H, H6), 9.83 (s, 1H, CHO); do (100 MHz, CDCl3) 23.9, 25.4, 31.6, 56.0, 76.9, 109.8, 113.2, 126.5, 129.7, 150.5, 153.0, 190.8; vmax 1133, 1263, 1504, 1581, 1680, 2857, 2933 cm−1.

Workup

  1. additiontreated
  2. customThe crude product was purified by flash chromatography with 10-15% EtOAc/petrol as eluent

Sources & evidence

ORD record
ord-d1124725cf774b6faf90e3720fcab6c3
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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