Hydrochloric Acid → HCID 71272420, compound

HRID 2204915Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=1[O:22][CH3:23].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:36][C:37]#[N:38])[CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33].CC(C)([O-])C.[K+].Cl>COC(C)(C)C.O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17](/[CH:18]=[C:36](/[C:28]2[CH:29]=[C:30]([O:34][CH3:35])[C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=2)\[C:37]#[N:38])=[CH:16][C:15]=1[O:22][CH3:23]

Participants

Conditions

Temperature: 54 °C

Procedure

7.1 g (22 mmol) of 4-[(11-hydroxyundecyl)oxy]-3-methoxybenzaldehyde, 5.0 g (24 mmol) of (3,4,5-trimethoxyphenyl)acetonitrile are dissolved in 50 mL of tert-butyl methyl ether. 0.49 g of potassium tert-butoxide are added under stirring and the mixture is heated to 54° C. After 18 h at 54° C., the reaction mixture is poured on 75 mL icy water under stirring. The pH is adjusted to 7 with 25% HCl. After 1 h stirring, the precipitate is filtered off, washed with water and dried at 40° C. under vacuum. 8.5 g of (2Z)-3-{4-[(11-hydroxyundecyl)oxy]-3-methoxyphenyl}-2-(3,4,5-trimethoxyphenyl)prop-2-enenitrile are obtained as a yellow solid (76% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.

Workup

stirringunder stirring
stirringAfter 1 h stirring
filtrationthe precipitate is filtered off
washwashed with water
customdried at 40° C. under vacuum

Sources & evidence

ORD record: ord-91a3034e1e5c4690a5929ae697aa2eb1
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09366906B2

Reaction notes

Loading…