Isovanillin → HCID 59333870, compound

HRID 1616765Notes

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=[CH:17][C:16](S(OCCCCC#C)(=O)=O)=[CH:15][CH:14]=1>>[CH2:17]([O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])[CH2:16][CH2:15][CH2:14][C:13]#[CH:12]

Participants

Reactant 2

HCID 12127Isovanillin

HCID 11097066HCID 11097066, compound

Product 1

HCID 59333870HCID 59333870, compoundYield 57%

Procedure

Isovanillin (0.78 g, 5.2 mmol) was alkylated using hex-5-ynyl 4-methylbenzenesulfonate (1.95 g, 7.73 mmol according to Procedure 4. The crude product was recystallised from EtOAc/petrol to provide 3-(hex-5-ynyloxy)-4-methoxybenzaldehyde (0.68 g, 57%) as a colourless crystalline solid; mp 66-67° C.; δH (400 MHz, CDCl3) 1.74 (p, J=7.2 Hz, 2H, CH2), 1.96-2.0 (m, 3H, CH2, C≡CH), 2.30 (td, J=7.2, 2.8 Hz, 2H, CH2C≡CH), 3.95 (s, 3H, OCH3), 4.11 (t, J=7.2 Hz, 2H, OCH2), 6.97 (d, J5,6=8.0 Hz, 1H, H5), 7.40 (d, J2,6=1.6 Hz, 1H, H2), 7.44 (dd, J5,6=8.0 Hz, J2,6=1.6 Hz, 1H, H6), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 18.1, 25.0, 28.0, 56.2, 68.4, 68.7, 83.9, 110.3, 110.6, 126.7, 130.1, 149.0, 154.9, 190.9; vmax 1018, 1263, 1582, 1679, 2933, 3238 cm−1.

Sources & evidence

ORD record: ord-35e7f64476604296a2d3366c2f3c1459
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765812B2

Reaction notes

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