Ethyl Acetate → HCID 18354140, compound

HRID 429012Notes

Reaction equation

HRID 429012 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([OH:11])[CH2:8][CH2:9][OH:10].[CH:12]([CH:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:13].C(OCC)(=O)C>O1CCCC1>[CH:12]([CH:14]([O:10][CH2:9][CH2:8][CH2:7][OH:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 104421,3-PropanediolHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 18354140HCID 18354140, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (23.07 g, 0.206 mol) was added to a stirred solution of 1,3-propanediol (44.92 g, 0.591 mol) in dry tetrahydrofuran (400 ml) under an atmosphere of nitrogen. The reaction mixture was stirred for 15 min then a solution of vinylbenzylchloride (mixture of meta and para isomers) (30.00 g, 0.197 mol) in dry tetrahydrofuran (100 ml) was added dropwise over 30 min. The reaction was heated at reflux overnight then the tetrahydrofuran was removed in vacuo and the residue taken-up in water (400 ml) and diethyl ether (400 ml). The organic phase was washed with water, dried (magnesium sulfate) and concentrated in vacuo to give a liquid. The liquid was purified by column chromatography over silica gel (eluent 3:1:petrol ether/ethyl acetate, then ethyl acetate) to give the title compound (30.59 g, 0.159 mol, 81%) as a straw colored liquid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customthe tetrahydrofuran was removed in vacuo
  4. washThe organic phase was washed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give a liquid
  8. customThe liquid was purified by column chromatography over silica gel (eluent 3:1

Sources & evidence

ORD record
ord-5f7b816f21354a50b378a439f47b343d
Source dataset
uspto-grants-2001_11
Patent number
US06316177B1

Reaction notes

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