Isovanillin → HCID 59333852, compound

HRID 1616769Notes

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

Participants

Reactant 2

HCID 12127Isovanillin

HCID 10966564pent-4-ynyl tosylate

Product 1

HCID 59333852HCID 59333852, compoundYield 83%

Procedure

Isovanillin (0.98 g, 6.4 mmol) was alkylated with pent-4-ynyl 4-methylbenzenesulfonate (2.3 g, 8.3 mmol) according to Procedure 4. The crude product was recystallised from EtOAc/petrol to provide 4-methoxy-3-(pent-4-ynyloxy)benzaldehyde (1.16 g, 83%) as a colourless crystalline solid; mp 73-74° C.; δH (400 MHz, CDCl3) 1.98 (t, J=2.4 Hz, 1H, CCH), 2.06 (p, J=7.0 Hz, 2H, CH2), 2.43 (td, J=7.0, 2.4 Hz, 2H, CH2C≡CH), 3.94 (s, 3H, OCH3), 4.18 (t, J=7.0 Hz, 2H, OCH2), 6.97 (d, J5′,6′=8.0 Hz, 1H, H5), 7.43 (s, 1H, H2), 7.45 (d, J5,6=8.0 Hz, 1H, H6), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 15.1, 27.9, 56.1, 67.3, 69.1, 83.2, 110.6, 110.7, 126.7, 130.0, 148.9, 154.9, 190.9; vmax 1025, 1263, 1584, 1665, 2849, 2936, 3254 cm−1.

Sources & evidence

ORD record: ord-3a9a94b59248441bb97687849d181eab
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765812B2

Reaction notes

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