Dicyclohexylcarbodiimide → 4-Benzyloxy-2-chloro-benzoic acid 4-(4-pentyl-phenoxycarbonyl)-phenyl ester

HRID 2356174Notes

Reaction equation

HRID 2356174 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31](=[O:39])[C:32]2[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)[CH2:20][CH2:21][CH2:22][CH3:23].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([C:32]2[CH:37]=[CH:36][C:35]([O:14][C:13](=[O:15])[C:12]3[CH:16]=[CH:17][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:10][C:11]=3[Cl:18])=[CH:34][CH:33]=2)=[O:39])=[CH:26][CH:25]=1)[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 50979854-(Benzyloxy)-2-chlorobenzoic acidHCID 136605894-Pentylphenyl 4-hydroxybenzoate

Product 1

HCID 684206604-Benzyloxy-2-chloro-benzoic acid 4-(4-pentyl-phenoxycarbonyl)-phenyl esterYield 93.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 50 mL of methylene chloride, 1.84 g (7.0 mmol) of 4-benzyloxy-2-chloro-benzoic acid, 1.90 g (6.7 mmol) of 4-hydroxy-benzoic acid 4-pentyl-phenyl ester, and 0.082 g (0.67 mmol) of 4-dimethylaminopyridine were dissolved. Then, 1.45 g (7.0 mmol) of dicyclohexylcarbodiimide was added while stirring the solution under argon. After being stirred for 8 hours under argon, the solution was filtered and the filtered liquid was concentrated. The residue was purified by silica-gel column chromatography. As a result, 3.3 g of a white solid was obtained.

Workup

  1. stirringAfter being stirred for 8 hours under argon
  2. filtrationthe solution was filtered
  3. concentrationthe filtered liquid was concentrated
  4. customThe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-2160bc1bbf2e4fe8aa347eeca0583e3f
Source dataset
uspto-grants-2010_07
Patent number
US07758932B2

Reaction notes

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