Carbon Tetrachloride → HCID 53957852, compound

HRID 1731558Notes

Reaction equation

HRID 1731558 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[CH:4]1[CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].[C:18](Cl)(Cl)(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][CH2:2][CH:3]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[CH:4]1[CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 6101p-Toluenesulfonic acidHCID 54450935HCID 54450935, compound

Product 1

HCID 53957852HCID 53957852, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

65.7 g (0.28 mole) of 6-(3-hydroxymethyl-bicyclo[2.2.1]hept-2-yl)-hex-5-enoic acid are heated under reflux in 220 ml of methanol and 600 ml of carbon tetrachloride with the addition of 6.0 g (0.03 mole) of p-toluenesulphonic acid, for 16 hours. The mixture is then washed 3 times with 500 ml of saturated aqueous sodium bicarbonate solution and twice with 500 ml of saturated aqueous sodium chloride solution. The mixture is dried over sodium sulphate and the solvents are then evaporated off in vacuo. 66.4 g (yield: 95%) of methyl 6-(3-hydroxymethyl-bicyclo-[2.2.1]hept-2-yl)-hex-5-enoate are obtained.

Workup

  1. washThe mixture is then washed 3 times with 500 ml of saturated aqueous sodium bicarbonate solution
  2. dry with materialThe mixture is dried over sodium sulphate
  3. customthe solvents are then evaporated off in vacuo

Sources & evidence

ORD record
ord-68b51ef6706f488aae115b143b1ad1cb
Source dataset
uspto-grants-1986_11
Patent number
US04622339

Reaction notes

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