Iodoethane → HCID 20289175, compound

HRID 381344Notes

Reaction equation

HRID 381344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=CC=1.[H-].[Na+].I[CH2:13][CH3:14].[O:15]1CC[CH2:17][CH2:16]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:15][CH2:16][CH3:17])=[CH:8][C:13]=1[CH3:14]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydride

Product 1

HCID 20289175HCID 20289175, compound

Procedure

To a solution of 1-chloro-4-hydroxymethylbenzene (14.2 g, 0.1 mol) in tetrahydrofuran (250 ml) was added sodium hydride as a 40% suspension in oil (4 g, 0.1 mol) portionwise under nitrogen. When effervescence ceased iodoethane (15.6 g, 0.1 mol) was added and the solution heated at reflux for 8 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with dilute aqueous sodium hydroxide and brine, then dried (MgSO4) and evaporated to dryness. The subtitle compound was obtained as a clear oil (17.3 g).

Workup

  1. additionwas added
  2. temperaturethe solution heated
  3. temperatureat reflux for 8 hours
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with dilute aqueous sodium hydroxide and brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5eb42fee362b4d488497b5d7f3ea7942
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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