3-(3-Chloro-2-hydroxypropoxy)benzaldehyde → 3-(3-Phthalimido-2-hydroxypropoxy)benzaldehyde

HRID 648182Notes

Reaction equation

HRID 648182 reaction equation
Cl[CH2:2][CH:3]([OH:14])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K]>CN(C)C=O.CCOCC>[C:15]1(=[O:25])[N:19]([CH2:2][CH:3]([OH:14])[CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=[O:10])[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

Participants

5

Reactant 2

HCID 128784723-(3-Chloro-2-hydroxypropoxy)benzaldehydeHCID 24194345Phthalimide potassium salt

Product 1

HCID 133240763-(3-Phthalimido-2-hydroxypropoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The distilled product from Example 1 (21.1 g, 0.098 mol) and potassium phthalimide (37 g, 0.20 mol) are dissolved in 100 ml of N,N-dimethylformamide and the mixture is heated 22 hours on a steam bath under N2. The mixture is cooled, diluted with 200 ml of ether and filtered. The filtrate is concentrated to remove ether and diluted to 500 ml with water to give the crystalline title product, 30.8 g, mp 122°-126°.

Workup

  1. temperaturethe mixture is heated 22 hours on a steam bath under N2
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customto remove ether
  6. additiondiluted to 500 ml with water

Sources & evidence

ORD record
ord-996d507d1e094a24afa05537fff04021
Source dataset
uspto-grants-1983_10
Patent number
US04411899

Reaction notes

Loading…