Vanillin → HCID 59333855, compound

HRID 1616747Notes

Reaction equation

HRID 1616747 reaction equation
Br[CH2:2][C:3]#[C:4][CH2:5]C.[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:18](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:18][O:15][C:14]1[CH:16]=[CH:17][C:9]([CH:8]=[O:7])=[CH:10][C:11]=1[O:12][CH2:13][C:2]#[C:3][CH2:4][CH3:5]

Participants

5

Reactant 3

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

Product 1

HCID 59333855HCID 59333855, compoundYield 96%

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. 4-Methoxy-3-(pent-2-ynyloxy)benzaldehyde (0.69 g, 96%) was obtained as a yellow crystalline solid; mp 38-39° C.; δH (400 MHz, CDCl3) 1.10 (t, J=7.6 Hz, 2H, CH2CH3), 2.20 (tq, J=7.6, 2.0 Hz, 3H, CH2CH3), 3.95 (s, 3H, OCH3), 4.79 (t, J=2.0 Hz, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.49 (dd, J5,6=8.0, J2,6=2.0 Hz, 1H, H6), 7.54 (d, J2,6=2.0 Hz, 1H, H2), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 12.5, 13.5, 56.1, 57.3, 73.4, 90.5, 110.7, 111.8, 126.9, 129.9, 147.6, 154.8, 190.8; vmax 1007, 1130, 1261, 1508, 1583, 1683, 2230, 2290, 2841, 2976 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-4e52ef20aeb3413ba9c26ac8cfbbac26
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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