Norbornadiene → 2,6-Bis(4-hydroxyphenylthio)bicyclo[2.2.1]heptane

HRID 1065606Notes

Reaction equation

HRID 1065606 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]12[CH2:15][CH:12]([CH:13]=[CH:14]1)[CH:11]=[CH:10]2>C1(C)C=CC=CC=1>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][CH:10]2[CH2:11][CH:12]3[CH2:15][CH:9]2[CH:14]([S:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH2:13]3)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 2401474-Mercaptophenol

Product 1

HCID 201500222,6-Bis(4-hydroxyphenylthio)bicyclo[2.2.1]heptane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sixty-six grams of 4-mercaptophenol, 100 ml. of toluene and 24.1 grams of 2,5-norbornadiene was heated to 70° C. and reacted 2.5 hours. After standing at room temperature for 16 hours, a white solid was filtered and washed with benzene-% sulfur, 17.9. Theoretical sulfur for 2,5 and/or 2,6-bis(4-hydroxyphenylthio)bicyclo[2.2.1]heptane is 18.0%. Melting point: 142°-146° C.

Workup

  1. customreacted 2.5 hours
  2. filtrationa white solid was filtered
  3. washwashed with benzene-% sulfur, 17.9

Sources & evidence

ORD record
ord-383206c5a46b433cb5c47ece65842e5d
Source dataset
uspto-grants-1982_05
Patent number
US04330462

Reaction notes

Loading…