Water → Phenol, 4,4'-tellurobis-

HRID 582956Notes

Reaction equation

HRID 582956 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Te:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][Si](C(C)(C)C)(C)C)=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].[K+].O.[OH-].[Na+]>CO.ClCCl.CCOCC>[Te:15]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 522689Potassium FluorideHCID 21226135HCID 21226135, compound

Product 1

HCID 9818288Phenol, 4,4'-tellurobis-Yield 76.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Silyl ether 4b (54.2 g, 0.1 mol) was taken up in methanol (200 mL) in a 500 mL round bottom flask. Potassium fluoride (11.6 g, 0.2 mol) was added, and the reaction mixture was heated to reflux for 1.5 h under argon. After the reaction mixture was cooled to room temperature, it was poured into rapidly stirring water (1.2 L), using additional methanol (20 mL) to facilitate the transfer. The pH was adjusted to 14 with 10% NaOH (approx. 40 mL), and the reaction mixture was filtered through Celite diatomaceous earth. The filtrate was transferred to a separatory funnel and washed twice with dichloromethane. The aqueous layer was transferred to a 2 L Erlenmeyer flask in an ice bath, and 25% aq. acetic acid was added to pH 6, resulting in formation of a cream-colored precipitate. The product was isolated by filtration, washed with water, and air dried, to give the crude product (29 g). It was adsorbed onto flash silica gel (150 mL) using ether. Vacuum chromatography on 1 L flash silica gel, eluting with dichloromethane then 1:4 ethyl acetate:dichloromethane gave the pure product. Trituration with dichloromethane gave, in two crops, pure 4c as a yellow solid (24 g, 76%). 1H NMR (CDCl3, 5 drops DMSO) d 8.77 (2H, s), 7.29 (4H, d, J=8.4), 6.47 (4H, d, J=8.4).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1.5 h under argon
  3. filtrationthe reaction mixture was filtered through Celite diatomaceous earth
  4. customThe filtrate was transferred to a separatory funnel
  5. washwashed twice with dichloromethane
  6. customThe aqueous layer was transferred to a 2 L Erlenmeyer flask in an ice bath
  7. addition25% aq. acetic acid was added to pH 6
  8. customresulting in formation of a cream-colored precipitate
  9. customThe product was isolated by filtration
  10. washwashed with water, and air
  11. customdried
  12. customto give the crude product (29 g)
  13. washVacuum chromatography on 1 L flash silica gel, eluting with dichloromethane
  14. custom1:4 ethyl acetate:dichloromethane gave the pure product

Sources & evidence

ORD record
ord-71288a1ae0a147c884ae39af9882a4fb
Source dataset
uspto-grants-1999_07
Patent number
US05928886

Reaction notes

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