Toluene → HCID 136029817, compound

HRID 2396075Notes

Reaction equation

HRID 2396075 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([NH2:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:20][C:21](=O)[CH2:22][C:23]([O:25][CH3:26])=[O:24].O1CCOCC1.C1(C)C=CC=CC=1>O>[CH3:26][O:25][C:23](=[O:24])[CH2:22][C:21]1[N:10]=[C:8]([C:7]2[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]([OH:14])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)[O:9][CH:20]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 312751,4-DioxaneHCID 36240Methyl 4-chloroacetoacetateHCID 6165023,5-Ditert-butyl-4-hydroxybenzamide

Product 1

HCID 136029817HCID 136029817, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,5-di-tert-butyl-4-hydroxybenzamide (5.0 g, 20.0 mmol), methyl 4-chloroacetoacetate (3.01 g, 20.0 mmol), dioxane (30 mL), and toluene (300 mL) was refluxed for 5 days, with continuous water removal (Dean Stark trap). The volatiles were removed in vacuo and the residue waspurified by flash chromatography on silica gel (eluting solvent: hexane/EtOAc 3/1) to give a brown viscous oil (3.2 g). Crystallization of the brown oil from ethyl ether (after cooling to 0° C.) gave a white solid (2.6 g, 38% yield), m.p. 126°-128° C.

Workup

  1. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-529e9a4d8e774e6ba486722fcd02438f
Source dataset
uspto-grants-1996_02
Patent number
US05491159

Reaction notes

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