Dicyclohexylcarbodiimide → 4-Pentylphenyl 4-(benzyloxy)benzoate

HRID 1442481Notes

Reaction equation

HRID 1442481 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH2:21][CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:18]([C:23]1[CH:24]=[CH:25][C:26]([O:14][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)=[CH:27][CH:28]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 269754-PentylphenolHCID 738804-(Benzyloxy)benzoic acid

Product 1

HCID 138105764-Pentylphenyl 4-(benzyloxy)benzoateYield 99.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

12.6 g (55.0 mmol) of 4-benzyloxy-benzoic acid, 8.2 g (50.0 mmol) of 4-pentylphenol and 0.61 g (5.0 mmol) of 4-dimethylaminopyridine were added to 150 mL of methylene chloride followed by the addition of 11.4 g (55.0 mmol) of dicyclohexylcarbodiimide while stirring in the presence of argon. After stirring for 6 hours in the presence of argon, the mixture was filtered followed by concentrating the filtrate. The residue was purified by silica gel column chromatography to obtain 18.7 g of a white solid.

Workup

  1. stirringAfter stirring for 6 hours in the presence of argon
  2. filtrationthe mixture was filtered
  3. concentrationby concentrating the filtrate
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f4aac16dfd44ca983f52c82166a4f8d
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Reaction notes

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