2-Methoxybenzaldehyde → 1-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan

HRID 2210051Notes

Reaction equation

HRID 2210051 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:10](=[O:11])[O:9][CH2:8]2.COC1C=CC=CC=1C=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:11][CH:10]1[C:12]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:8][O:9]1.[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

6

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 109865837-methoxy-3H-isobenzofuran-1-one

Product 2

HCID 136136891-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furanHCID 19598060Methyl 2E-3-(2-hydroxymethyl-6-methoxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

1-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan (1.08 g), which was prepared with using 7-methoxyphthalide which was synthesized with using 2-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

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

Sources & evidence

ORD record
ord-bf4ee21eb7b94f47ab3758936b7b45a2
Source dataset
uspto-grants-1995_10
Patent number
US05457122

Reaction notes

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