Methylparaben → Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate

HRID 583673Notes

Reaction equation

HRID 583673 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].CCOC(/N=N/C(OCC)=O)=O.O[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CN(C=O)C.CCOCC>[C:8]1(=[O:9])[N:4]([CH2:3][CH2:2][O:1][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[C:5](=[O:14])[C:6]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]12

Participants

8

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 7679064Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(2-hydroxyethyl)phthalimide (Aldrich, 19-1, 6.36 g, 33 mmol) and DEAD (5.7 mL, 36 mmol) in 25 mL THF and 10 mL DMF was added to a solution of methyl 4-hydroxybenzoate (1-2, 5.00 g, 33 mmol) and Ph3P (9.53 g, 36 mmol) in 100 mL THF during 1 h. After an additional hour the reaction was diluted with ether, washed twice with water, then 1N NaOH and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica gel, CH2Cl2) provided 19-2 as a white solid.

Workup

  1. washwashed twice with water
  2. dry with material1N NaOH and brine, dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-38fe269c9aa64d9ca0e14a938a912982
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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