Water → 4-(4-Methoxystyryl)benzyl alcohol

HRID 262200Notes

Reaction equation

HRID 262200 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH:7]=[CH:8][C:9]2[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH:7]=[CH:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 53892329Ethyl 4-(4-methoxystyryl)benzoate

Product 1

HCID 544979264-(4-Methoxystyryl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Ethyl 4-(4-methoxystyryl)benzoate (67 g.) in 600 ml. of tetrahydrofuran was gradually added to a suspension of 12 g. of lithium aluminum hydride in 300 ml. of tetrahydrofuran at such a rate to maintain gentle reflux. The reaction mixture was heated at reflux for two hours, then cooled and 24 ml. of water in 24 ml. of tetrahydrofuran added slowly. The mixture was stirred for one hour, heated to reflux temperature and filtered hot through a steam-jacketed funnel. The solvent was removed from the filtrate to give 55 g. of 4-(4-methoxystyryl)benzyl alcohol, m.p. 200°-202° C. when recrystallized from ethanol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for two hours
  3. temperaturecooled
  4. temperatureheated
  5. temperatureto reflux temperature
  6. filtrationfiltered hot through a steam-jacketed funnel
  7. customThe solvent was removed from the filtrate
  8. customto give 55 g
  9. customof 4-(4-methoxystyryl)benzyl alcohol, m.p. 200°-202° C. when recrystallized from ethanol

Sources & evidence

ORD record
ord-32574ddcf30a4521b2ee020bb9313625
Source dataset
uspto-grants-1979_05
Patent number
US04153719

Reaction notes

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