2-Mercaptoethanol → HCID 21539895, compound

HRID 1076279Notes

Reaction equation

HRID 1076279 reaction equation
OC[CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2.[SH:10][CH2:11][CH2:12][OH:13].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCOCC1>[OH:13][CH2:12][CH2:11][S:10][CH:3]1[CH:4]2[CH2:9][CH:7]([CH2:6][CH2:5]2)[CH2:8]1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 6547AzobisisobutyronitrileHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanol

Product 1

HCID 21539895HCID 21539895, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

In a nitrogen atmosphere, to a stirred solution of 12.4 grams (0.1 mole) of 2-hydroxymethyl-5-norbornene in 100 ml of dioxane was added in one portion 17.2 grams (0.22 mole) of 2-mercaptoethanol. The temperature rose from 25° to 50°. The mixture was then heated at 70° for 6.3 hours during which time a solution of 1.6 grams of α,α'-azobisisobutyronitrile in 20 ml of dioxane was added in portions. After standing overnight, the dioxane solvent and excess 2-mercaptoethanol were removed under reduced pressure. The residue was distilled to give the 2-methylol- 5 or 6-(2'-hydroxyethylthio)norbornane intermediate as a viscous oil with a boiling point of 140°-142°/0.05 mm in a yield of 15.0 grams (74%).

Workup

  1. customrose from 25° to 50°
  2. additionwas added in portions
  3. customthe dioxane solvent and excess 2-mercaptoethanol were removed under reduced pressure
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-9188e2f712f6459cb10edbdbabe81569
Source dataset
uspto-grants-1976_05
Patent number
US03956361

Reaction notes

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