Vanillin → HCID 43185077, compound

HRID 1616758Notes

Reaction equation

HRID 1616758 reaction equation
Br[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[O:9]=[CH:10][C:11]1[CH:19]=[CH:18][C:16]([OH:17])=[C:13]([O:14][CH3:15])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH:3]1([CH2:2][O:17][C:16]2[CH:18]=[CH:19][C:11]([CH:10]=[O:9])=[CH:12][C:13]=2[O:14][CH3:15])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 43185077HCID 43185077, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromomethylcyclohexane (0.78 mL, 4.2 mmol) was added to a suspension of vanillin (0.43 g, 2.8 mmol) and potassium carbonate (1.17 g, 8.47 mmol) in EtOH (7.0 mL) and treated according to Procedure 3 for 64 h. 4-Cyclohexylmethoxy-3-methoxybenzaldehyde (0.65 g, 93%) was obtained as a yellow oil; δH (400 MHz, CDCl3) 1.05 (m, 2H, CH2), 1.15-1.36 (m, 4H, CH2), 1.73 (m, 2H, CH2), 1.87-1.98 (m, 2H, CH2, CH), 3.88 (d, J=6.0 Hz, 2H, OCH2), 3.92 (s, 3H, OCH3), 6.95 (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), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 25.6, 26.4, 29.8, 37.3, 56.1, 74.5, 109.3, 111.4, 126.8, 129.8, 149.9, 154.4, 190.9; vmax 1133, 1265, 1508, 1586, 1683, 2853, 2925 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-9a8c422006e549528b34a9b904c7b1f6
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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