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

HRID 1657053
Notes
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Reaction equation

HRID 1657053 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.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].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.[OH:19][CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([O:14][CH3:13])[C:16]=1/[CH:3]=[CH:12]/[C:10]([O:9][CH3:8])=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 109865837-methoxyisobenzofuran-1(3H)-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 (108 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-a9d616a9cf924ec68f810527282ea978
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05256686

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes