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

HRID 568298Notes

Reaction equation

HRID 568298 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

To the reactor of Example 1 was added 66 grams of 4-mercaptophenol, 100 ml. toluene and 24.1 grams of 2,5-norbornadiene. The mixture was reached for 2.5 hours at 70° C. The mixture was cooled to ambient temperature and after 16 hours the white solid was filtered and washed with benzene. The product contained 17.9% sulfur and had a melting point of 142°-146° C.

Workup

  1. filtrationwas filtered
  2. washwashed with benzene

Sources & evidence

ORD record
ord-024bc365c30b4935946d0dcc4db61bb3
Source dataset
uspto-grants-1988_03
Patent number
USRE032618

Reaction notes

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