4,4'-Dihydroxybiphenyl → HCID 22719191, compound

HRID 1581896Notes

Reaction equation

HRID 1581896 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.[Cl:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.O1CCCC1>[Cl:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 71124,4'-DihydroxybiphenylHCID 11776TriphenylphosphineHCID 900121-Octanol, 8-chloro-HCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 22719191HCID 22719191, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (3.5 g; 20 mmol) and tetrahydrofuran (10 ml) was added dropwise at 0° C. to a solution of 4,4′-dihydroxybiphenyl (7.4 g; 40 mmol), 8-chloro-1-octanol (3.3 g; 20 mmol), triphenylphosphine (5.2 g; 20 mmol) and tetrahydrofuran (120 ml) and stirred at room temperature 72 h. The reaction mixture was added to water (400 ml) and extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with water (2×150 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuo. The residue (19.2 g) was purified by flash chromatography on a silica gel column using a toluene/ethyl acetate mixture (95:5) as eluent, to give 2.6 g (40%) of 4′-[(8-chlorooctyl)oxy]-4-biphenylol.

Workup

  1. extractionextracted with ethyl acetate (3×150 ml)
  2. washThe combined organic layers were washed with water (2×150 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customThe residue (19.2 g) was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-dc749c5e73a84058ab88dedfd392530b
Source dataset
uspto-grants-2004_05
Patent number
US06733690B1

Reaction notes

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