N-(hydroxymethyl)phthalimide → Phthalimidomethyl acetoacetate

HRID 231825

Reaction equation

HRID 231825 reaction equation
[OH:1][CH2:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13].[CH3:14][C:15]1[O:21]C(C)(C)O[C:17](=[O:18])[CH:16]=1>C1(C)C=CC=CC=1>[C:17]([O:1][CH2:2][N:3]1[C:4](=[O:13])[C:5]2=[CH:12][CH:11]=[CH:10][CH:9]=[C:6]2[C:7]1=[O:8])(=[O:18])[CH2:16][C:15]([CH3:14])=[O:21]

Participants

4

Reactant 2

HCID 8354N-(hydroxymethyl)phthalimideHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 13636318Phthalimidomethyl acetoacetateYield 97.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10.0 g (0.056 mol) of N-(hydroxymethyl)phthalimide and 8.02 g (0.056 mol) of 2,2,6-trimethyl-1,3-dioxen-4-one in 100 ml of toluene was refluxed for 24 hours under nitrogen. Recrystallization in ethyl acetate gives 14.3 g (97%) of an off-white solid: mp 106°-109° C.; NMR (CDCl3) 7.6 (4H,m), 5.6 (2H,s), 3.4 (2H,s), 2.18 (3H,s);

Workup

  1. customRecrystallization in ethyl acetate

Sources & evidence

ORD record
ord-a4b5f533bb0d42aab6cb22fa1ea960d1
Source dataset
uspto-grants-1989_07
Patent number
US04849436

Linked notes

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