Water → 4-(4-Phenylbutoxy)styrene

HRID 1603927Notes

Reaction equation

[CH2:1]([Li])CCC.[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.C(OCC)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[CH2:1])=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyltriphenylphosphonium bromide (4.98 g, 13.9 mmol) in anhydrous tetrahydrofuran (130 ml) at 0° C. and under inert atmosphere was added with a 1.6M butyl lithium solution in hexane (8.69 ml) and the mixture was left under stirring at 0° C. for 2 h. After that, a solution of 4-(4-phenylbutoxy)benzaldehyde (2.5 g, 9.84 mmol) in tetrahydrofuran (10 ml) was added and the mixture was left under stirring at room temperature for 36 h, then carefully added with water (20 ml) and extracted with ethyl ether (4×50 ml). The organic extracts were dried and the solvents were evaporated off under reduced pressure. The resulting crude was purified by chromatography through a silica gel column, eluting with petroleum ether:ethyl ether, 95:5, thereby recovering 4.20 g of the title compound (62% yield).

Workup

waitthe mixture was left
waitthe mixture was left
stirringunder stirring at room temperature for 36 h
extractionextracted with ethyl ether (4×50 ml)
customThe organic extracts were dried
customthe solvents were evaporated off under reduced pressure
customThe resulting crude was purified by chromatography through a silica gel column
washeluting with petroleum ether

Sources & evidence

ORD record: ord-8d51799efc6a428b910662c3291a4696
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990142

Reaction notes

Loading…