Vanillin → HCID 59333872, compound

HRID 1616745Notes

Reaction equation

HRID 1616745 reaction equation
Br[CH2:2][C:3]#[C:4][CH2:5][CH3:6].[O:7]=[CH:8][C:9]1[CH:17]=[CH:16][C:14]([OH:15])=[C:11]([O:12][CH3:13])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][O:12][C:11]1[CH:10]=[C:9]([CH:17]=[CH:16][C:14]=1[O:15][CH2:2][C:3]#[C:4][CH2:5][CH3:6])[CH:8]=[O:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 853991-Bromopent-2-yne

Product 1

HCID 59333872HCID 59333872, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromopent-2-yne (0.67 mL, 6.6 mmol) was added to a suspension of vanillin (0.50 g, 3.3 mmol) and potassium carbonate (1.37 g, 9.85 mmol) in acetone (5.0 mL) and treated according to Procedure 3. 3-Methoxy-4-(pent-2-ynyloxy)benzaldehyde (0.60 g, 84%) was obtained as a yellow crystalline solid; mp 47-50° C.; δH (400 MHz, CDCl3) 1.11 (t, J=7.6 Hz, 2H, CH2CH3), 2.20 (tq, J=7.6, 2.4 Hz, 3H, CH2CH3), 3.93 (s, 3H, OCH3), 4.83 (t, J=2.4 Hz, 2H, OCH2), 7.13 (d, J5,6=8.0 Hz, 1H, H5), 7.42 (s, 1H, H2), 7.45 (d, J5,6=8.0 Hz, H6), 9.86 (s, 1H, CHO); δC (100 MHz, CDCl3) 12.5, 13.4, 56.0, 57.3, 73.1, 90.7, 109.2, 112.3, 126.4, 130.5, 149.9, 152.5, 190.9; vmax 997, 1136, 1263, 1508, 1586, 1682, 2230, 2298, 2845, 2932 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-3483374d4cc3417da1ba2bc377b31d87
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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