N-(4-Hydroxyphenyl)Phthalimide → Methyl 7-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]-2,2-dimethylheptanoate

HRID 648987Notes

Reaction equation

HRID 648987 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])=[CH:4][CH:3]=1.O(C)[Na].[CH3:22][C:23]([CH3:34])([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]I)[C:24]([O:26][CH3:27])=[O:25]>CN(C=O)C>[O:18]=[C:9]1[C:10]2[C:11](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:13])[N:8]1[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:23]([CH3:22])([CH3:34])[C:24]([O:26][CH3:27])=[O:25])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 252281N-(4-Hydroxyphenyl)PhthalimideHCID 14153168Methyl 7-iodo-2,2-dimethylheptanoateHCID 178418582HCID 178418582, compound

Product 1

HCID 14153169Methyl 7-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]-2,2-dimethylheptanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[p-Hydroxyphenyl]phthalimide (5.0 g) described in Example 1 was dissolved in 100 ml of DMF and 1.13 g of NaOCH3 was added. The solution was stirred at room temperature for one-half hour, then 6.25 g of methyl 2,2-dimethyl-7-iodoheptanoate was added dropwise. The mixture was stirred at room temperature overnight and then heated at reflux for two hours and concentrated on rotary evaporator. H2O (100 ml) was added and a solid was obtained. The product was extracted with EtOAc leaving the insoluble starting material behind. Concentration of the ethyl acetate solution followed by recrystallization of the resulting solid from isopropyl ether gave the purified product; mp 82°-3° C.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. temperatureheated
  3. temperatureat reflux for two hours
  4. concentrationconcentrated on rotary evaporator
  5. additionH2O (100 ml) was added
  6. customa solid was obtained
  7. extractionThe product was extracted with EtOAc leaving the
  8. customConcentration of the ethyl acetate solution followed by recrystallization of the resulting solid from isopropyl ether
  9. customgave the purified product

Sources & evidence

ORD record
ord-ecc46022bff34e7b893d5c141d74ad87
Source dataset
uspto-grants-1988_04
Patent number
US04737512

Reaction notes

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