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Water → 4-(Hexyloxy)phenyl 4-(benzyloxy)benzoate

HRID 64523
Notes
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Reaction equation

HRID 64523 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]([O:24][C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C1(N=C=NC2CCCCC2)CCCCC1.O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:26][CH:27]=2)=[O:14])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 293544-HexyloxyphenolHCID 738804-(Benzyloxy)benzoic acid

Product 1

HCID 672168004-(Hexyloxy)phenyl 4-(benzyloxy)benzoateYield 70.3%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

4-(benzyloxy)benzoic acid (20.0 g, 87.6 mmol), 4-(hexyloxy)phenol (17.0 g, 87.6 mmol), N,N′-dicyclohexylcarbodiimide (21.7 g, 105 mmol) and 4-dimethylaminopyridine (535 mg, 4.38 mmol) were dissolved in 300 mL of methylene chloride. The resulting solution was stirred for 3 hours at room temperature. Then, 300 mL of pure water was added thereto, and then the resulting liquid was filtered to remove insoluble matters. Thereafter, the obtained solution was subjected to separation operation, and the resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. After methylene chloride was distilled off, the resulting solid matter was washed with methanol. Thereby, a white solid compound, 4-(hexyloxy)phenyl 4-(benzyloxy)benzoate (24.9 g) was obtained.

Workup

  1. filtrationthe resulting liquid was filtered
  2. customto remove insoluble matters
  3. customThereafter, the obtained solution was subjected to separation operation
  4. washthe resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter methylene chloride was distilled off
  7. washthe resulting solid matter was washed with methanol

Sources & evidence

ORD record
ord-2cfd64a566634aa5bc81b63d6e3f3d0a
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09449732B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes