Ethanol → HCID 86749003, compound

HRID 2399989Notes

Reaction equation

[CH2:1]([OH:3])[CH3:2].N1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:10](Cl)(=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)(Cl)Cl>[C:1]([O:28][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][OH:28])(=[O:3])[CH2:2][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:9]/[CH:8]=[CH:7]\[CH2:6]/[CH:5]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

1,30-Triacontadiol (38) (2.5 g, 5.5 mmol) was dissolved in dry, ethanol free chloroform at 60° C. under nitrogen and treated with pyridine (0.49 ml; 6.05 mmol). The resulting solution was treated with a solution of linoleoyl chloride (39) (1.64 g; 5.5 mmol) in chloroform (20 ml) over a twenty minute period and then maintained at 60° C. for a further thirty minutes, then cooled, diluted with chloroform, washed with water three times, dried, filtered and evaporated. The crude product obtained in this manner was purified on silica (30 g). Elution with chloroform gives the title compound (40) as a white solid (1.73 g; 44%).

Workup

customin dry
temperaturecooled
washwashed with water three times
customdried
filtrationfiltered
customevaporated
customThe crude product obtained in this manner
customwas purified on silica (30 g)
washElution with chloroform

Sources & evidence

ORD record: ord-d003bd42af0e4135902def8d9b91515c
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05451691

Reaction notes

Loading…