3-Phenylprop-2-En-1-Ol → HCID 54180613, compound

HRID 1368010Notes

Reaction equation

HRID 1368010 reaction equation
[OH-].[Na+].[CH2:3]([CH:5]1[O:7][CH2:6]1)Br.[CH2:8]([OH:17])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([O:17][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:5]1[O:7][CH2:6]1

Participants

5

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 14798Sodium HydroxideHCID 18430Epibromohydrin

Product 1

HCID 54180613HCID 54180613, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

To a four-neck 1000 ml round bottom flask, equipped with a mechanical stirrer, thermometer, and condenser, were added 50% w/w aqueous sodium hydroxide (“NaOH”) (250 ml), epibromohydrin (56 g, 400 mmol), and tetrabutylammoniumhydrogen sulfate (“TBAHS”) (5.2 g, 14.9 mmol). The mixture was stirred at room temperature for a period of time of about 20 minutes. To the mixture was added cinnamyl alcohol (50 g, 365 mmol), drop-wise over a period of time of about 60 minutes. The reaction was conducted at ice/water temperatures, and was allowed to continue overnight with stirring. Once the reaction was complete, the mixture was cooled and ice cold water (500 ml) was slowly added. The quenched reaction was allowed to stir for a period of time of about 30 minutes and then twice extracted with diethyl ether (250 ml). The organic portion was separated and twice washed with brine (250 ml), dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness in vacuo. Crude CGE was obtained as a clear amber liquid (67.0 g), which was distilled in vacuo (119-135° C. at 820 mTorr) to provide CGE (48.1 g, 247.8 mmol), as a clear colorless liquid. G.C. 98.0% (retention time 8.10 min.). 1H NMR (CDCl3) δ7.2-7.4 (br m, 5, C6H5), 6.65 (d, 1, —CH═), 6.25 (m, 1, ═CH—), 4.2 (br m, 2, CH2), 3.75 and 3.20 (d, 2, CH2), 3.45 (m, 1, OCH), 2.8 and 2.6 (d, 2, OCH2). FT-IR (neat) 3081, 3057, 3025, 2999, 2922, 2855, 1495, 1448, 1253, 1115, 969, 902, 855, 746, 694.

Workup

  1. customTo a four-neck 1000 ml round bottom flask, equipped with a mechanical stirrer
  2. waitdrop-wise over a period of time of about 60 minutes
  3. waitto continue overnight
  4. stirringwith stirring
  5. temperaturethe mixture was cooled
  6. customThe quenched reaction
  7. stirringto stir for a period of time of about 30 minutes
  8. extractiontwice extracted with diethyl ether (250 ml)
  9. customThe organic portion was separated
  10. washtwice washed with brine (250 ml)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-265315f5ea7f474eba4bf88d33872063
Source dataset
uspto-grants-2003_06
Patent number
US06572980B1

Reaction notes

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