Benzoate → 2-(4-Chloro-3-nitrophenylcarboxy)ethyl 3,5-di-t-butyl-4-hydroxybenzoate

HRID 845365Notes

Reaction equation

HRID 845365 reaction equation
C([O-])(=[O:8])C1C=CC=CC=1.C(C1C=[C:16]([CH:30]=C(C(C)(C)C)C=1O)[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)=[O:18])(C)(C)C.[C:38]([C:42]1[CH:43]=[C:44]([CH:48]=[C:49]([C:52]([CH3:55])([CH3:54])[CH3:53])[C:50]=1[OH:51])[C:45](Cl)=[O:46])([CH3:41])([CH3:40])[CH3:39]>ClCCl>[C:38]([C:42]1[CH:43]=[C:44]([CH:48]=[C:49]([C:52]([CH3:55])([CH3:54])[CH3:53])[C:50]=1[OH:51])[C:45]([O:8][CH2:30][CH2:16][C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)=[O:18])=[O:46])([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 242BenzoateHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 201310134-Chloro-3-nitrophenyl 3,5-di-t-butyl-4-hydroxybenzoate

Product 1

HCID 201310052-(4-Chloro-3-nitrophenylcarboxy)ethyl 3,5-di-t-butyl-4-hydroxybenzoateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the benzoate (13.7 g, 55.9 mmole) from (a) and 3,5-di-t-butyl-4-hydroxybenzoyl chloride (15.0 g, 55.9 mmole) in dichloromethane (50 ml) were heated under reflux for 42 hours. The solvent was removed by rotary evaporation, and the residue crystallized from 10% toluene in hexane, to give the product (22.9 g, 86%) as a white solid. m.p. 106°-108° C.

Workup

  1. temperatureunder reflux for 42 hours
  2. customThe solvent was removed by rotary evaporation
  3. customthe residue crystallized from 10% toluene in hexane

Sources & evidence

ORD record
ord-fa7b7142c1844d36b5313aa177ac3e16
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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