Hydrochloric Acid → 1-(2-Chloroethyl)isochroman

HRID 1417792Notes

Reaction equation

HRID 1417792 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Cl:5][CH2:6][CH2:7][CH:8](OCC)[O:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>[N+](C)([O-])=O>[Cl:5][CH2:6][CH2:7][CH:8]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][O:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 10728903(2-(3-Chloro-1-ethoxypropoxy)ethyl)benzene

Product 1

HCID 106079661-(2-Chloroethyl)isochroman

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Aluminum trichloride (17.44 g, 0.131 mol) is added, in aliquots over a period of 5-10 min, to an ice-cooled solution of [2-(3-chloro-1-ethoxypropoxy)ethyl]benzene (LXIII, PREPARATION 1, 28.87 g, 0.119 mol) in nitromethane (150 ml). After 30 min, hydrochloric acid (4N) is added and the mixture is partitioned between ether and saline. The organic phase, which contains nitromethane, is dried over magnesium sulfate and carefully concentrated under reduced pressure. The nitromethane/product mixture is then extracted six times with hexane and the hexane extracts are concentrated and chromatographed on silica gel eluting with ether/hexane (5/95). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 2.23, 2.36, 2.71, 2.97, 3.68, 3.79, 4.10, 4.93 and 7.06-7.23 δ.

Workup

  1. customthe mixture is partitioned between ether and saline
  2. dry with materialis dried over magnesium sulfate
  3. concentrationcarefully concentrated under reduced pressure
  4. extractionThe nitromethane/product mixture is then extracted six times with hexane
  5. concentrationthe hexane extracts are concentrated
  6. customchromatographed on silica gel eluting with ether/hexane (5/95)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d76a623a9f584187b2e78a3f1e488010
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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