Vanillin → 4-Methoxy-3-[(prop-2-yn-1-yl)oxy]benzaldehyde

HRID 1616743Notes

Reaction equation

HRID 1616743 reaction equation
[CH2:1](Br)[C:2]#C.[O:5]=[CH:6][C:7]1[CH:15]=[CH:14][C:12]([OH:13])=[C:9]([O:10][CH3:11])[CH:8]=1.[C:16](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:16][O:13][C:12]1[CH:14]=[CH:15][C:7]([CH:6]=[O:5])=[CH:8][C:9]=1[O:10][CH2:11][C:1]#[CH:2]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 27633274-Methoxy-3-[(prop-2-yn-1-yl)oxy]benzaldehydeYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (2.90 mL, 80% w/v, 19.7 mmol) was added to a suspension of vanillin (2.00 g, 13.1 mmol) and potassium carbonate (5.46 g, 39.4 mmol) in acetone (20 mL) and treated according to Procedure 3. 4-Methoxy-3-propargyloxybenzaldehyde (2.01 g, 80%) was obtained as a colourless crystalline solid; mp 66-67° C.; δH (400 MHz, CDCl3) 2.54 (t, J=2.4 Hz, 1H, C≡CH), 3.95 (s, 3H, OCH3), 4.81 (d, J=2.4 Hz, 1H, OCH2), 7.00 (d, J5,6=8.4 Hz, 1H, H5), 7.50-7.53 (m, 2H, H2, H6), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 56.1, 56.6, 76.4, 77.6, 110.9, 111.9, 127.3, 129.9, 147.3, 154.9, 190.6; HRMS (ESI) Calculated for C11H10O3 [M+H]+ 191.0703. found 191.0704; vmax 1014, 1130, 1261, 1584, 1678, 2119, 2841, 2932, 3262 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-7f322dd74790493792e4981917d0aacd
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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