Ethyl Acetate → 2-(2-Chloro-4-nitrophenyl)ethanol

HRID 1019731Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[Cl:14].[Li+].[BH4-].[NH4+].[Cl-].CCOC(C)=O>C1COCC1.O>[Cl:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[CH2:4][CH2:3][OH:2]

Participants

Conditions

Temperature: 0 °C

Procedure

(2-Chloro-4-nitro-phenyl)-acetic acid methyl ester (17 g, 74 mmol) was dissolved in dry THF (85 mL) and cooled to 0° C. A solution of LiBH4 in THF (2M, 75 mL, 148 mmol) was added drop-wise at 0° C. and the reaction mixture was maintained for 5 hours at RT. After completion of reaction, NH4Cl solution (2 mL) was added to the reaction mixture which was then stirred for 15 minutes. EtOAc (170 mL) and water (85 mL) were added and stirred for 10 minutes. The separated aqueous layer was extracted with EtOAc (85 mL), then the combined organic extracts were dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil. The oil was purified by column chromatography on neutral silica gel using 5-10% EtOAc in hexane to give the title compound (10 g, 55%).

Workup

temperaturethe reaction mixture was maintained for 5 hours at RT
additionwas added to the reaction mixture which
stirringstirred for 10 minutes
extractionThe separated aqueous layer was extracted with EtOAc (85 mL)
dry with materialthe combined organic extracts were dried (Na2SO4)
customevaporated under reduced pressure
customto give a yellow oil
customThe oil was purified by column chromatography on neutral silica gel using 5-10% EtOAc in hexane

Sources & evidence

ORD record: ord-baa6b5ebc5854313af34e67641ca20ea
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716287B2

Reaction notes

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