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

HRID 482298Notes

Reaction equation

HRID 482298 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=C(C=CC=1)C=O.C1(P(=CC(OC)=O)(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

Participants

5

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 109865837-methoxy-3H-isobenzofuran-1-one

Product 1

HCID 136136891-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

1Hydroxy-7-methoxy-1,3-dihydrobenzo[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

  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-3c136f74521f4e87b8ce46b1c969868a
Source dataset
uspto-grants-1998_08
Patent number
US05795914

Reaction notes

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