Phenol → HCID 66588561, compound

HRID 1596853Notes

Reaction equation

HRID 1596853 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(C(F)(F)F)(=O)=O.[CH2:16]1[CH:20]2[CH:21]3[CH:25]=[CH:24][CH:23]([CH:19]2[CH:18]=[CH:17]1)[CH2:22]3.[OH-].[Na+]>CN1C(=O)CCC1>[CH2:16]1[CH:20]2[CH:21]3[CH:25]=[CH:24][CH:23]([CH:19]2[CH:18]=[CH:17]1)[CH2:22]3.[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 996Phenol3×HCID 6492Dicyclopentadiene2×HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 66588561HCID 66588561, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A multi-neck 5 liter flask fitted with condenser, overhead stirrer and thermometer was charged with: 2858 g of phenol (containing 0.03% water); 2.4 g triflic acid; and 7.2 g NMP and under nitrogen blanket was heated to 100° C. A solution of 912 g dicyclopentadiene (6.89 moles, Ultrene 99) and 45 g phenol (total phenol is 2903 g) was added over 2 hours at 100° C.±0.5%. The dicyclopentadiene to phenol mole ratio charged in this example is 0.22. After 65 minutes at 100° C. catalyst was neutralized with a dilute solution of sodium hydroxide to a solution pH of 5.6 (2.5 g solution with 25 ml methanol). Phenol (2270 g) and product (1457 g) were recovered as in the following Example 30 using steam sparging with 200 ml water over 1.25 hours. Product was characterized as follows: phenol 0.24%; Mw/Mn 172/149, does not include the SEC peak at 95±1 (Mw/Mn of 131/115 includes the SEC peak at 95±1); viscosity of 550 cps; refractive index of 1.5711 (25.4° C.).

Workup

  1. customA multi-neck 5 liter flask fitted with condenser
  2. customPhenol (2270 g) and product (1457 g) were recovered as in the following Example 30 using steam
  3. customsparging with 200 ml water over 1.25 hours
  4. customrefractive index of 1.5711 (25.4° C.)

Sources & evidence

ORD record
ord-40f824d3c8f94ed2ac47197b530de0de
Source dataset
uspto-grants-2001_09
Patent number
US06291723B1

Reaction notes

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