2-Phenylethanol → (2-(3-Chloro-1-ethoxypropoxy)ethyl)benzene

HRID 1417791Notes

Reaction equation

HRID 1417791 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH2:6][Cl:7])[CH3:2].C(O)C[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CS(O)(=O)=O>[N+](C)([O-])=O>[Cl:7][CH2:6][CH2:5][CH:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH2:2][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 6395Methanesulfonic AcidHCID 962173-Chloro-1,1-diethoxypropane

Product 1

HCID 10728903(2-(3-Chloro-1-ethoxypropoxy)ethyl)benzene

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

3-Chloropropionaldehyde diethyl acetal (LXII, 30.66 g, 0.184 mol) is added to an ice-cooled solution of phenethyl alcohol (XLV, 20.44 g, 0.167 mol) in nitromethane (50 ml) is added and methanesulfonic acid (1.61 g, 0.0167 mol). After 30 min the ice bath is removed and the mixture is allowed to stir overnight. The mixture is then warmed in a water bath at approximately 40°-50° under reduced pressure for 10-20 min (no appreciable removal of nitromethane occurs but there is some further reaction observed). The mixture is partitioned between ethyl ether and saline, the layers are separated and the organic phase is dried over magnesium sulfate and concentrated under reduced pressure. The crude material is stored overnight in the refrigerator and then chromatographed on silica gel eluting with hexane and then ethyl acetate/hexane (2/98). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.20, 2.05, 2.87, 3.43-3.86, 4.69 and 7.24 δ.

Workup

  1. additionis added
  2. customAfter 30 min the ice bath is removed
  3. temperatureThe mixture is then warmed in a water bath at approximately 40°-50° under reduced pressure for 10-20 min (
  4. customno appreciable removal of nitromethane
  5. customThe mixture is partitioned between ethyl ether and saline
  6. customthe layers are separated
  7. dry with materialthe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. waitThe crude material is stored overnight in the refrigerator
  10. customchromatographed on silica gel eluting with hexane
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-89969d6bb3654e6daf888e71e665f4f9
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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