Water → ST025572

HRID 1761417Notes

Reaction equation

HRID 1761417 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=[CH:5][CH:4]=1.O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[C:9]([O:11][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 113702-Methoxybenzoic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 716774ST025572Yield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-anisic acid (1.0 g), N-hydroxysuccinimide (0.76 g) and water-soluble carbodiimide hydrochloride (1.39 g) were dissolved in methylene chloride (15 ml), and the solution was stirred overnight at room temperature. The precipitate was removed by filtration. The mother liquor was concentrated under reduced pressure, and the residue was crystallized from isopropanol to give 1.47 g of N-(2-methoxybenzoyloxy)succinimide (mp. 180°-182° C.).

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationThe mother liquor was concentrated under reduced pressure
  3. customthe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-184b570e39cc450aabcdaaebe8ba4a44
Source dataset
uspto-grants-1989_05
Patent number
US04826814

Reaction notes

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