Vanillin → HCID 59333899, compound

HRID 1616752Notes

Reaction equation

HRID 1616752 reaction equation
Br[CH2:2][C:3]#[C:4][CH3:5].[O:6]=[CH:7][C:8]1[CH:16]=[CH:15][C:13]([OH:14])=[C:10]([O:11]C)[CH:9]=1.[C:17](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:11][C:10]1[CH:9]=[C:8]([CH:16]=[CH:15][C:13]=1[O:14][CH3:17])[CH:7]=[O:6])[C:3]#[C:4][CH3:5]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyne

Product 1

HCID 59333899HCID 59333899, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromobut-2-yne (0.37 mL, 4.0 mmol) was added to a suspension of vanillin (0.56 g, 3.7 mmol) and potassium carbonate (1.82 g, 11.0 mmol) in acetone (10 mL) and treated according to Procedure 3. 3-(But-2-ynyloxy)-4-methoxybenzaldehyde (0.72 g, 96%) was obtained as a pale yellow crystalline solid; mp 81-83° C.; δH (400 MHz, CDCl3) 1.84 (t, J=2.0 Hz, 3H, CH3), 3.95 (s, 3H, OCH3), 4.77 (q, J=2.0 Hz, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.49 (dd, J5,6=8.4, J2,6=2.0 Hz, 1H, H6), 7.51 (d, J2,6=2.0 Hz, 1H, H2), 9.86 (s, 1H, CHO); δC (100 MHz, CDCl3) 3.7, 56.1, 57.1, 73.2, 84.7, 110.6, 111.4, 126.9, 129.9, 147.6, 154.8, 190.8; vmax 1003, 1259, 1506, 1583, 1681, 2226, 2297, 2841, 2916 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-77837d08007848b2b8fafcb875f1a38f
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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