Hydrochloric Acid → 3-(2-Phenyl-vinyl)-benzyl alcohol

HRID 1680041Notes

Reaction equation

HRID 1680041 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H][H].Cl>O1CCCC1>[C:13]1([CH:12]=[CH:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[CH2:4][OH:3])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 53642270Ethyl 3-(2-phenylethenyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 544260303-(2-Phenyl-vinyl)-benzyl alcoholYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

10 g (0.03 mol) of 3-(2-phenyl-vinyl)-benzoic acid ethyl ester, dissolved in 50 ml of dry tetrahydrofuran, were added dropwise to 2.5 g of lithium aluminium hydride in 50 ml of anhydrous tetrahydrofuran at 25°-30° C., whilst stirring thoroughly. The reaction mixture was then subsequently stirred at 22° C. for 10 hours and then cooled to 0° C. and ice-water was added dropwise, whilst stirring, until no further evolution of hydrogen could be observed (60 ml). The precipitate which had formed was dissolved by adding 30 ml of concentrated hydrochloric acid dropwise, and the reaction mixture was then extracted twice with 100 ml of toluene each time. The organic phase was separated off and dried over sodium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by subjecting the product to brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 5 g (61% of theory) of 3-(2-phenyl-vinyl)-benzyl alcohol were obtained as a yellow oil with the refractive index nD22 : 1.6286 (isomer mixture with a cis proportion of about 90%). ##STR62##

Workup

  1. stirringThe reaction mixture was then subsequently stirred at 22° C. for 10 hours
  2. customThe precipitate which had formed
  3. dissolutionwas dissolved
  4. extractionthe reaction mixture was then extracted twice with 100 ml of toluene each time
  5. customThe organic phase was separated off
  6. dry with materialdried over sodium sulphate
  7. distillationthe solvent was distilled off under a waterpump vacuum
  8. customLast residues of solvent were removed
  9. distillationto brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-477fbe692e524d8097356f3edb042971
Source dataset
uspto-grants-1981_06
Patent number
US04271186

Reaction notes

Loading…