Bisphenol A → HCID 178447687, compound

HRID 1106216Notes

Reaction equation

HRID 1106216 reaction equation
[P:1]([O-:15])([O:9]CC(C)(C)C)[O:2]C1C=CC=CC=1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)([CH3:25])[CH3:24])=[CH:19][CH:18]=1.C[O-].[Na+]>>[CH2:20]([PH:1]([OH:15])([OH:9])[OH:2])[C:23]([CH3:26])([CH3:25])[CH3:24].[CH2:20]([PH:1]([OH:15])([OH:9])[OH:2])[C:23]([CH3:26])([CH3:25])[CH3:24].[OH:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)([CH3:25])[CH3:24])=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 6623Bisphenol AHCID 10942334Sodium MethoxideHCID 22491470HCID 22491470, compound

Product 1

HCID 178447687HCID 178447687, compound

Conditions

Temperature
130 °C

Procedure

A mixture of 272 g (1.2 mole) of phenyl neopentyl phosphite, 126 g (0.55 mole) of bisphenol-A (BPA) and 1 g of sodium methoxide were heated together in a round-bottom flask. The temperature of the reaction vessel was raised to 130° C. and a vacuum was applied. Phenol was distilled over at 90° C. head temperature at 35 mm. The temperature was raised slowly to 160° C. and the vacuum increased to 0.2 mm Hg to remove any remaining phenol and unreacted phenyl neopentyl phosphite. The proton NMR spectrum of the product recovered showed the methyl protons at 0.77, 1.30 and 1.65 δ (18.1 hydrogens), the methylene protons at 3.67 and 4.30 δ (7.2 hydrogens) and the aromatic protons from 6.7-7.3 δ (8.7 hydrogens). This bisphosphite had the following structure: ##STR3##

Workup

  1. temperaturewere heated together in a round-bottom flask
  2. distillationPhenol was distilled over at 90° C. head temperature at 35 mm
  3. temperatureThe temperature was raised slowly to 160° C.
  4. temperaturethe vacuum increased to 0.2 mm Hg
  5. customto remove any remaining phenol and unreacted phenyl neopentyl phosphite
  6. customThe proton NMR spectrum of the product recovered

Sources & evidence

ORD record
ord-f285740936be4a22a0fd2f2906a7f2fc
Source dataset
uspto-grants-1982_01
Patent number
US04312803

Reaction notes

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