4,4'-Dihydroxybiphenyl → HCID 19873709, compound

HRID 2220000Notes

Reaction equation

HRID 2220000 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C1COCC1>[OH:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:15][C:14](=[O:16])[C:13]3[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:18][CH:17]=3)=[CH:28][CH:27]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 10868DicyclohexylcarbodiimideHCID 172314-(Octyloxy)benzoic acid

Product 1

HCID 19873709HCID 19873709, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4.5 g (0.018 mol) of 4-Octyloxy-benzoic acid, 7.0 g (0.038 mol) of 4,4′-Dihydroxy biphenyl and 0.46 g (3.7 mmol) of DMAP are dissolved in 65 mL of dry THF and 4.4 g (0.021 mol) of DCC is added. After stirring for 18 h at room temperature, the suspension is filtered. The residue is dissolved in a hot solution of hexane:CHCl3:THF=2:2:1 and after cooling to room temperature, the precipitate is filtered off. The recrystallisation is repeated until the TLC indicates pure white product (3.7 g, 49% yield).

Workup

  1. filtrationthe suspension is filtered
  2. dissolutionThe residue is dissolved in a hot solution of hexane
  3. temperatureCHCl3:THF=2:2:1 and after cooling to room temperature
  4. filtrationthe precipitate is filtered off
  5. customThe recrystallisation

Sources & evidence

ORD record
ord-32df3cdc6a5a49b9993d8eb52b19b64f
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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