Hydrochloric Acid → Benzenepropanol

HRID 845893Notes

Reaction equation

HRID 845893 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](O)(=[O:16])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>C(OCC)C>[CH2:7]([OH:16])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 87842-Propenoic acid, 3-phenyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 31234BenzenepropanolYield 32.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

Into a solution of 12 g (0.31 mole) of lithium aluminum hydride in 100 ml of anhydrous diethyl ether was added dropwise a solution prepared by dissolving 37 g (0.25 mole) of cinnamic acid in 100 ml of anhydrous diethyl ether at a temperature of 0° to 20° C. After completion of the dropwise addition of the solution, the mixture was further agitated for additional 30 minutes at 20° C. and then admixed with 100 ml of a 10% hydrochloric acid followed by phase separation. The organic solution taken by phase separation was subjected to evaporation of the ether and then distilled under reduced pressure to give 11 g of dihydrocinnamyl alcohol, which yield was 31% of the theoretical value, but neither cinnamyl alcohol nor cinnamic aldehyde could be obtained.

Workup

  1. customprepared
  2. additionAfter completion of the dropwise addition of the solution
  3. customfollowed by phase separation
  4. customThe organic solution taken by phase separation
  5. customwas subjected to evaporation of the ether
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c38a656922e94735a2de3a48f05e1ad5
Source dataset
uspto-grants-1988_07
Patent number
US04760196

Reaction notes

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