3-Methoxybenzaldehyde → Methyl 2E-3-(2-hydroxymethyl-6-methoxyphenyl)acrylate

HRID 1533949Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:10](=O)[O:9][CH2:8]2.COC1C=C(C=CC=1)C=O.C1(P(=[CH:42][C:43]([O:45][CH3:46])=[O:44])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[OH:9][CH2:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:12]=1/[CH:10]=[CH:42]/[C:43]([O:45][CH3:46])=[O:44]

Participants

Conditions

Temperature: 50 °C

Procedure

1-Hydroxy-7-methoxy-1,3-dihgydrobenzo[c]furan (1.08 g), which was prepared with using 7-methoxyphthalide which was synthesized with using 3-methoxybenzaldehyde by the method described in Journal of Organic Chemistry, 1980, 45, 1835-1838, was dissolved in chloroform (20 ml). Methyl (triphenylphosphoranylidene)acetate (2.68 g) was added to the solution. The mixture was stirred for 40 min. at 50° C. A temperature of the reaction mixture was down to room temperature. The reaction solution was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (1.25 g) having the following physical data.

Workup

customwas down to room temperature
customThe reaction solution was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-25ede0036f15408c8249c7a2b481f88b
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05086065

Reaction notes

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