Water → HCID 20072040, compound

HRID 981370Notes

Reaction equation

HRID 981370 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:18][O-:19].[Na+].F[C:22]1[C:26]([F:28])([F:27])[C:25]([F:30])([F:29])[C:24]([F:32])([F:31])[C:23]=1F.[OH2:34]>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:22]3[C:26]([F:28])([F:27])[C:25]([F:30])([F:29])[C:24]([F:32])([F:31])[C:23]=3[O:19][C:18]3[CH:13]=[CH:12][C:11]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([OH:34])=[CH:3][CH:4]=4)([CH3:10])[CH3:9])=[CH:16][CH:15]=3)=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6623Bisphenol AHCID 11212PerfluorocyclopenteneHCID 10942334Sodium Methoxide

Product 1

HCID 20072040HCID 20072040, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

45.6 of bisphenol A (0.2 mol) were dissolved in 100 ml of methanol with warming and 36 g of a 30% strength by weight sodium methoxide solution were added. The mixture was evaporated to dryness on a rotary evaporator, 61 g of monosodium bisphenol A remaining. This was dissolved in 100 ml of dimethylformamide, 21.2 g of perfluorocyclopentene (0.1 mol) were added at 5° C. in the course of 60 minutes, then the mixture was warmed to room temperature and stirred at room temperature for 18 hours. It was then warmed to 70° C. for 2 hours. The mixture was then stirred into 200 ml of water and the organic phase was separated off. The latter was taken up in methylene chloride, and the solution was washed with 100 ml of water, then with 50 ml of 5% strength by weight hydrochloric acid and then again with 100 ml of water and then dried. After stripping off the solvent on a rotary evaporator and drying in the vacuum of an oil pump at 100° C., 53 g of a glass-like, transparent residue remained, which corresponds to 90.7% of theory. The 19F nuclear magnetic resonance spectrum showed characteristic bands at δ=-36.1 ppm and at δ=-51.5 ppm, measured against trifluoroacetic acid as external standard.

Workup

  1. temperaturewith warming
  2. customThe mixture was evaporated to dryness on a rotary evaporator, 61 g of monosodium bisphenol A remaining
  3. dissolutionThis was dissolved in 100 ml of dimethylformamide
  4. temperatureIt was then warmed to 70° C. for 2 hours
  5. customthe organic phase was separated off
  6. washthe solution was washed with 100 ml of water
  7. dry with materialwith 50 ml of 5% strength by weight hydrochloric acid and then again with 100 ml of water and then dried
  8. customon a rotary evaporator
  9. customdrying in the vacuum of an oil pump at 100° C.

Sources & evidence

ORD record
ord-2386525c91b74b2fac44a2272f9e48b2
Source dataset
uspto-grants-1991_02
Patent number
US04990633

Reaction notes

Loading…