Acetone → (E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate

HRID 1956021Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].CC(C)=[O:19]>O.[N+]([O-])([O-])=O.[Ag+]>[OH:19][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11]

Participants

Conditions

Temperature: 2 °C

Procedure

(E)-Methyl 2-[2-(bromomethyl)phenyl]-3-methoxypropenoate (15 g) was dissolved in acetone (200 ml) and the solution was cooled to 2° C. A solution of silver nitrate (22.35 g) in water (200 ml) at 4° C. was added to this. The temperature rose to 12° C. After stirring for 40 minutes the green/grey precipitate which had formed was filtered off and the filtrate partitioned between water and diethyl ether. The diethyl ether layer was washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to give an oil which was purified by chromatography on silica gel, eluting with diethyl ether, to give (E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate as a viscous oil (6.33 g, 54%). 1H NMR (CDCl3): 2.3(t,1H), 3.7(s,3H) 3.8(s,3H), 4.5(d,2H), 7.1(m,1H), 7.2-7.4(m,2H), 7.5(m,1H), 7.6(s,1H) ppm.

Workup

customrose to 12° C
customhad formed
filtrationwas filtered off
customthe filtrate partitioned between water and diethyl ether
washThe diethyl ether layer was washed with brine
dry with materialdried over anhydrous sodium sulphate
customevaporated under reduced pressure
customto give an oil which
customwas purified by chromatography on silica gel
washeluting with diethyl ether

Sources & evidence

ORD record: ord-493bc1ed11a649a4a75dbf8c2f3b0634
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05777162

Reaction notes

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