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4-Hydroxybenzaldehyde → 4-[3-(1,3-Dioxoisoindol-2-yl)propoxy]benzaldehyde

HRID 325691
Notes
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Reaction equation

HRID 325691 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>CN(C)C=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:13][CH2:14][CH2:15][N:16]2[C:20](=[O:21])[C:19]3[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]2=[O:26])=[CH:3][CH:4]=1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydride

Product 1

HCID 19890894-[3-(1,3-Dioxoisoindol-2-yl)propoxy]benzaldehydeYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzaldehyde (24.4 g) and sodium hydride (4.8 g) in dry dimethylformamide (400 ml) were stirred at room temperature for 3 h. N-(3-Bromopropyl)phthalimide (55.0 g) was added and the reaction was stirred for a further 5 h. The mixture was poured onto ice and the resulting white solid was recrystallized from a mixture of dichloromethane and cyclohexane to yield the title compound (42.2 g) m.p. 120°-1°. TLC silica, ethyl acetate, Rf 0.7.

Workup

  1. additionThe mixture was poured onto ice
  2. customthe resulting white solid was recrystallized from a mixture of dichloromethane and cyclohexane

Sources & evidence

ORD record
ord-77005f307d2f4f5583abcf459f32064e
Source dataset
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04442110

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes