Phenol → 2,4-Divinylphenol

HRID 1086131Notes

Reaction equation

HRID 1086131 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]=[CH:9]C1C=CC=CC=1.[C:16]1(C)C=CC(S(O)(=O)=O)=C[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:8]=[CH:9][C:4]1[CH:5]=[CH:6][C:1]([OH:7])=[C:2]([CH:16]=[CH2:17])[CH:3]=1

Participants

5

Reactant 4

HCID 996Phenol2×HCID 6101p-Toluenesulfonic acidHCID 7501StyreneHCID 10340Sodium Carbonate

Product 1

HCID 185418432,4-Divinylphenol

Procedure

1 mol of phenol was reacted with 2.2 moles of styrene in the presence of 0.5% of paratoluene sulphonic acid based on the phenol, until the temperature rose to 135° C. The reactants were held at this temperature for 15 minutes, then neutralized with sodium carbonate solution, washed with twice the phenol weight of water; half the phenol weight of toluene was added, the mix agitated, and then allowed to settle. The top water layer was drawn off, the toluene was distilled off, and the product filtered to ensure clarity. A yield of 338% by weight basis of the original phenol content was obtained. The product had a refractive index of 1.603 and a viscosity of 5000 cP at 25° C. (as measured by a Brookfield viscometer, model RVF, spindle 4, speed 20 rpm, at 25° C.).

Workup

  1. customrose to 135° C
  2. washwashed with twice the phenol weight of water
  3. additionhalf the phenol weight of toluene was added
  4. distillationthe toluene was distilled off
  5. filtrationthe product filtered

Sources & evidence

ORD record
ord-302754af12954179aeaf19fa7a785dea
Source dataset
uspto-grants-1991_07
Patent number
US05027890

Reaction notes

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