Sodium Iodide → HCID 15006939, compound

HRID 2165183Notes

Reaction equation

HRID 2165183 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[I-].[Na+].Cl[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>CN(C)C=O.CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7638MonobenzoneHCID 748286-Chloro-1-hexanolHCID 10942334Sodium Methoxide

Product 1

HCID 15006939HCID 15006939, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 106.0 g (0.53 mole) of p-benzyloxyphenol (Eastman), 28.6 g (0.53 mole) sodium methoxide (MCB) and about 2 g of sodium iodide in 600 ml of dimethylformamide is stirred for 5 minutes, after which 73 g (0.53 mole) of 6-chlorohexan-1-ol (MCB) is added, and the mixture is refluxed with stirring. The methanol formed in the reaction is allowed to distill off. After 2 hours reflux, the mixture is diluted with ice and water, 500 ml of 10% potassium hydroxide is added, and the resultant precipitate collected and dried. The solid is combined with 1 liter of butanone, refluxed and filtered. The residue is cooled, whereupon the desired product crystallizes out. The solid product is stirred with 1 liter of acetone at room temperature, the mixture is filtered to separate additional insoluble by-product, the acetone boiled off and replaced with methanol, and the methanolic solution cooled to crystallize out the desired product, m.p. 94-97° C.

Workup

  1. temperaturethe mixture is refluxed
  2. stirringwith stirring
  3. distillationto distill off
  4. temperatureAfter 2 hours reflux
  5. additionthe mixture is diluted with ice and water, 500 ml of 10% potassium hydroxide
  6. additionis added
  7. customthe resultant precipitate collected
  8. customdried
  9. temperaturerefluxed
  10. filtrationfiltered
  11. temperatureThe residue is cooled, whereupon the desired product
  12. customcrystallizes out
  13. stirringThe solid product is stirred with 1 liter of acetone at room temperature
  14. filtrationthe mixture is filtered
  15. customto separate additional insoluble by-product
  16. temperaturethe methanolic solution cooled
  17. customto crystallize out the desired product, m.p. 94-97° C.

Sources & evidence

ORD record
ord-55d9cd0905bd4af082678c8b039924b8
Source dataset
uspto-grants-1990_07
Patent number
US04939173

Reaction notes

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