Acetic Acid → HCID 14147965, compound

HRID 274069Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]\[N+:11]([O-:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+].C(O)(=O)C.[Cl-].[Na+]>O1CCOCC1.C(O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of (Z)-1-(3-methoxyphenyl)-2-nitroethene (33.85 g) in 1,4-dioxane (315 ml) was added dropwise to an efficiently stirred suspension of sodium borohydride (15.77 g) in a mixture of 1,4-dioxane (315 ml) and ethanol (98 ml) over a period of 0.5 hour while maintaining a temperature of 30° C. After stirring for 2 hours, the resultant slurry was diluted with ice water (393 ml) and the excess sodium borohydride was decomposed with 50% aqueous acetic acid (47.4 ml). To the solution, sodium chloride (68 g) and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by distillation under reduced pressure to give 1-methoxy-3-(2-nitroethyl)benzene (23.62 g).

Workup

customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
distillationThe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record: ord-06dcae5850eb40f1a79735621668f9a1
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05387710

Reaction notes

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