Isovanillin → HCID 24704043, compound

HRID 1616773Notes

Reaction equation

[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.[CH3:12][C:13]1C=CC(S(OCCC#C)(=O)=O)=[CH:15][CH:14]=1>>[CH2:15]([O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])[CH2:14][C:13]#[CH:12]

Participants

Reactant 2

HCID 12127Isovanillin

HCID 2720203-Butynyl p-toluenesulfonate

Product 1

HCID 24704043HCID 24704043, compoundYield 35%

Procedure

Isovanillin (0.95 g, 6.2 mmol) was alkylated with but-3-ynyl 4-methylbenzenesulfonate (2.1 g, 9.4 mmol) according to Procedure 4. The crude product was recystallised from EtOAc/petrol to provide 3-(but-3-ynyloxy)-4-methoxybenzaldehyde (0.44 g, 35%) as a colourless crystalline solid; mp 63-65° C.; δH (400 MHz, CDCl3) 2.06 (t, J=2.8 Hz, 1H, C≡CH), 2.76 (td, J=7.2, 2.8 Hz, 2H, CH2C≡CH), 3.96 (s, 3H, OCH3), 4.22 (t, J=7.2 Hz, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.43 (d, J2,6=1.4 Hz, 1H, H2), 7.45 (dd, J5,6=8.0, J2,6=1.4 Hz, 1H, H6), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 19.4, 56.2, 67.0, 70.3, 79.8, 110.9, 111.2, 127.1, 130.1, 148.4, 154.9, 190.7; vmax 1015, 1124, 1231, 1586, 1675, 2821, 3305 cm−1.

Sources & evidence

ORD record: ord-5b92b156af5c4762af55028df644a51b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765812B2

Reaction notes

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