Vanillin → 3-Methoxy-4-prop-2-ynyloxy-benzaldehyde

HRID 1616735Notes

Reaction equation

HRID 1616735 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[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(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][O:10][C:9]1[CH:8]=[C:7]([CH:15]=[CH:14][C:12]=1[O:13][CH2:3][C:2]#[CH:1])[CH:6]=[O:5]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 31440663-Methoxy-4-prop-2-ynyloxy-benzaldehydeYield 86.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (219 mL, 80% w/v, 1.48 mol) was added to a suspension of vanillin (150 g, 0.986 mol) and potassium carbonate (408 g, 2.96 mol) in acetone (1.50 L) and treated according to Procedure 3. 3-Methoxy-4-propargyloxybenzaldehyde (162 g, 86%) was obtained as yellow crystalline solid; mp 95° C.; δH (400 MHz, CDCl3) 2.56 (t, J=2.5 Hz, 1H, C≡CH), 3.95 (s, 3H, OCH3), 4.86 (d, J=2.5 Hz, 2H, OCH2), 7.14 (d, J5,6=6.8 Hz, 1H, H5), 7.44 (d, J2,6=1.4 Hz, 1H, H2), 7.47 (dd, J5,6=6.8, J2,6=1.4 Hz, 1H, H6), 9.87 (s, 1H, CHO); δC (100 MHz, CDCl3) 56.0, 56.6, 77.2, 77.4, 109.4, 112.5, 126.3, 130.9, 150.0, 152.1, 190.9; HRMS (ESI) Calculated for C11H10O3 [M+H]+ 191.0703. found 191.0706; vmax 1006, 1130, 1259, 1586, 1677, 2119, 2845, 2932, 3266 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-d21ac45432c24f8db6ecab92530f1720
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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