Pyridine → 2-Methylbutyl 4-(4'-carbobenzoxyoxybenzoyloxy)benzoate

HRID 1199865

Reaction equation

HRID 1199865 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([O:8][CH2:9][CH:10]([CH3:13])[CH2:11][CH3:12])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:22]([O:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O1CCCC1>[C:22]([O:32][C:33]1[CH:34]=[CH:35][C:36]([C:37]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH:10]([CH3:13])[CH2:11][CH3:12])=[O:7])=[CH:14][CH:15]=2)=[O:38])=[CH:40][CH:41]=1)([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl esterHCID 197340544-Carbobenzoxyoxybenzoyl chloride

Product 1

HCID 197340602-Methylbutyl 4-(4'-carbobenzoxyoxybenzoyloxy)benzoateYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 16 mmol (3.3 g) of the 2-methylbutyl p-hydroxybenzoate obtained in 1.(2) in a solvent mixture of 20 ml of THF (tetrahydrofuran) and 40 ml of pyridine was cooled, and to the solution was added dropwise a THF solution of 10 mmol (2/9 g) of the 4-carbobenzoxyoxybenzoyl chloride obtained in 1.(4). The temperature was gradually returned to room temperature, and then the mixture was stirred for 8 hours. After conclusion of the reaction, the reaction solution and purified by column chromatography to obtain 2.9 g of 2-methylbutyl 4-(4'-carbobenzoxyoxybenzoyloxy)benzoate [m.p.: 64.4°-65.4° C⟧ (Yield: 63%)

Workup

  1. temperaturewas cooled
  2. customobtained in 1.(4)
  3. customwas gradually returned to room temperature
  4. customAfter conclusion of the reaction
  5. customthe reaction solution and purified by column chromatography

Sources & evidence

ORD record
ord-c451ceebfc764dc88c729636dff54986
Source dataset
uspto-grants-1990_02
Patent number
US04904065

Linked notes

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