Vanillin → HCID 59333859, compound

HRID 1616750Notes

Reaction equation

HRID 1616750 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][CH3:12])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:14][C:13]1[CH:15]=[CH:16][C:8]([CH:7]=[O:6])=[CH:9][C:10]=1[O:11][CH3:12])[C:3]#[C:4][CH3:5]

Participants

5

Reactant 3

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

Product 1

HCID 59333859HCID 59333859, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromobut-2-yne (0.36 mL, 4.0 mmol) was added to a suspension of vanillin (0.55 g, 3.6 mmol) and potassium carbonate (1.79 g, 10.9 mmol) in acetone (10 mL) and treated according to Procedure 3. 4-(But-2-ynyloxy)-3-methoxybenzaldehyde (0.70 g, 95%) was obtained as a pale yellow crystalline solid; mp 90-92° C.; δH (400 MHz, CDCl3) 1.84 (t, J=2.2 Hz, 3H, CH3), 3.93 (s, 3H, OCH3), 4.81 (q, J=2.2 Hz, 2H, OCH2), 7.12 (d, J5,6=8.4 Hz, 1H, H5), 7.42 (d, J2,6=2.0 Hz, 1H, H2), 7.45 (dd, J5,6=8.4, J2,6=2.0 Hz, 1H, H6), 9.86 (s, 1H, CHO); δC (100 MHz, CDCl3) 4.0, 56.2, 57.5, 73.2, 85.2, 109.4, 112.4, 126.7, 130.7, 150.1, 152.7, 191.2; vmax 991, 1259, 1504, 1586, 1679, 2226, 2302, 2833, 2921 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-60f1de7e6dec45ed94fd1e5d026b9f22
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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