5,5'-Dichloro-3,3',6,6'-tetramethyl-2,2'-biphenol → 3,3',6,6'-Tetramethyl-2,2'-biphenol

HRID 2297081Notes

Reaction equation

HRID 2297081 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[C:5]([C:10]2[C:11]([OH:19])=[C:12]([CH3:18])[C:13](Cl)=[CH:14][C:15]=2[CH3:16])=[C:4]([CH3:20])[CH:3]=1>C(O)C.O.C(N(CC)CC)C.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:16][C:15]1[CH:14]=[CH:13][C:12]([CH3:18])=[C:11]([OH:19])[C:10]=1[C:5]1[C:6]([OH:9])=[C:7]([CH3:8])[CH:2]=[CH:3][C:4]=1[CH3:20]

Participants

7

Reactant 1

HCID 185446535,5'-Dichloro-3,3',6,6'-tetramethyl-2,2'-biphenol

Product 1

HCID 113569233,3',6,6'-Tetramethyl-2,2'-biphenolYield 94%

Reagents, catalysts & solvents 5

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A sample of purified 5,5′-dichloro-3,3′,6,6′-tetramethyl-2,2′-biphenol (15.0 g, 48.4 mmol) was dissolved in 100 mL of ethanol containing 10 mL of water and 20 mL of triethylamine. This solution was added to 1.0 g (dry weight basis) of moist 20% Pd(OH)2/C (Pearlman's catalyst) and hydrogenated at 50 psig for 2 hours at ambient temperature. The product was isolated by filtration of catalyst, concentration, dissolution of the residue in EtOAc, washing with water, and concentration to dryness to give 11.0 g (94%) of product, mp 110-113° C. 1H-NMR (CDCl3) δ 1.95 (s, 3H), 2.25 (s, 3H), 4.71 (s, 1H), 6.81 (d, 1H, J=7.5 Hz), 7.10 (d, 1H, J=7.5 Hz).

Workup

  1. washwashing with water, and concentration to dryness

Sources & evidence

ORD record
ord-0a803ca9449d4700944b027e2e4ec7f7
Source dataset
uspto-grants-2002_12
Patent number
US06489517B1

Reaction notes

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