Phenol → HCID 18961418, compound

HRID 1708325Notes

Reaction equation

HRID 1708325 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([NH2:14])(=[O:13])[CH2:9][C:10]([CH3:12])=O.F[C:16](F)(F)[C:17]([OH:19])=O.B(F)(F)F>CCOCC>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([C:10]([C:1]2[CH:6]=[CH:16][C:17]([OH:19])=[CH:3][CH:2]=2)([CH3:12])[CH2:9][C:8]([NH2:14])=[O:13])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6356Boron trifluoride2×HCID 6422Trifluoroacetic acidHCID 80077Acetoacetamide

Product 1

HCID 18961418HCID 18961418, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 63.3 g, (0.6735 mol), of phenol, 8.51 g, (0.0842 mol) of acetoacetamide and 40 ml of trifluoroacetic acid was placed in a 500 ml, 3-necked flask equipped with a gas inlet tube and a condenser. The mixture was stirred under nitrogen and BF3 gas was introduced while the reaction temperature was maintained at 20° C. A total of 17.6 g of BF3 gas was added over a period of 3 hr. The reaction mixture was diluted with 200 ml of ether and the ether solution was washed with water three times. The ether and excess phenol were removed under vacuum maintaining the temperature below 90° C. When the viscous residue was dissolved in 50 ml of methanol, a white precipitate formed. The white solid was filtered, washed with cold methanol and dried. Based on method of preparation, there was obtained 3,3-bis(4-hydroxyphenyl)butyramide referred to below as "bisphenol". The yield of the product was 13.47 g (59.0%), mp=216°-216.5° C. 1H nmr (ppm in DMSO-d6): C-CH3 (s)1.71(3), CH2 (s) 2.79(2), NH2 6.50 & 6.85(2), Haarom (d) 6.95(J=8.55Hz (4), Hbarom (d) 6.85 (J=8.54Hz) (4), OH(s) 9.12 (2) . 13C nmr(ppm in DMSO-d6): C1 139.94, C2 127.83, C3 114.49, C4 154.94, C5 43.68, C6 28.25, C7 46. 83 C8 172. 56.

Workup

  1. customequipped with a gas inlet tube and a condenser
  2. washthe ether solution was washed with water three times
  3. customThe ether and excess phenol were removed under vacuum
  4. temperaturemaintaining the temperature below 90° C
  5. dissolutionWhen the viscous residue was dissolved in 50 ml of methanol
  6. customa white precipitate formed
  7. filtrationThe white solid was filtered
  8. washwashed with cold methanol
  9. customdried
  10. customBased on method of preparation

Sources & evidence

ORD record
ord-99de3088762747b8927f194f316c800d
Source dataset
uspto-grants-1994_10
Patent number
US05357033

Reaction notes

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