4-Pentylbenzoyl chloride → Benzoic acid, 2-chloro-4-[(4-pentylbenzoyl)oxy]-, 4-pentylphenyl ester

HRID 918552Notes

Reaction equation

HRID 918552 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:3]=1[C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=1)=[O:5].[CH2:23]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH2:24][CH2:25][CH2:26][CH3:27]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:28]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:29][CH:30]=2)[CH:19]=[CH:18][C:3]=1[C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 1708124-Pentylbenzoyl chlorideHCID 3084934Benzoic acid, 2-chloro-4-hydroxy-, 4-pentylphenyl ester

Product 1

HCID 7168197Benzoic acid, 2-chloro-4-[(4-pentylbenzoyl)oxy]-, 4-pentylphenyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-pentylphenyl 2-chloro-4-hydroxybenzoate (0.0075 mole) prepared as in Example 1 and p-pentylbenzoyl chloride (0.0075 mole) in pyridine (35 ml.) is stirred at room temperature for 5 hours. The reaction mixture is then poured into ice-water. The product is filtered and washed with water to give 4-n-pentylphenyl 2-chloro-4-(4-pentylbenzoyloxy)benzoate (3.1 g., 84%), m.p. 38°-122°C. The analytical sample, m.p. 39°-122°C is obtained by chromatography on Florisil and crystallization from ethanol. The theoretical values calculated for C30H33ClO4 and the values actually found are as follows:

Workup

  1. filtrationThe product is filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-94a72464ff1c410290107e9bab34700b
Source dataset
uspto-grants-1976_07
Patent number
US03971824

Reaction notes

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