Hydrochloric Acid → (4-Propylphenyl)methanol

HRID 493035Notes

Reaction equation

HRID 493035 reaction equation
O1CCCC1.C[O:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O.CO>[CH2:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][OH:7])=[CH:14][CH:13]=1)[CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 12861010Methyl 4-propylbenzoateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 2760472(4-Propylphenyl)methanolYield 98.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dried tetrahydrofuran (50 ml) in which 10.4 g (58.4 mmol) of 4-n-propylbenzoic acid methyl ester synthesized in step (i) was dissolved was dropwise added to 50 ml of dried tetrahydrofuran containing suspension of lithium aluminium hydride (1.54 g: 40.5 mmol) at a temperature of not more than 10° C. with cooling with ice, and reaction was carried out at a room temperature overnight. After the completion of the reaction, an excess amount of lithium aluminium hydride was reacted with methanol with cooling with ice. Next water and an aqueous solution of hydrochloric acid were successively added to the reaction mixture, and the resultant was extracted with hexane. After the hexane phase was washed with water, hexane was removed from the hexane phase to give 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol.

Workup

  1. temperaturewith cooling with ice, and reaction
  2. customAfter the completion of the reaction
  3. temperaturewith cooling with ice
  4. extractionthe resultant was extracted with hexane
  5. washAfter the hexane phase was washed with water, hexane
  6. customwas removed from the hexane phase

Sources & evidence

ORD record
ord-a6779d30ec104bc38523bca87f1e820f
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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