Water → 3-(2-Propoxyphenyl)-1-propanol

HRID 1169488Notes

Reaction equation

HRID 1169488 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[CH:13]=[CH:14][C:15](OCC)=[O:16])[CH2:8][CH3:9].O.[OH-].[Na+]>C(OCC)C>[CH2:7]([O:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[CH2:13][CH2:14][CH2:15][OH:16])[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70025127Ethyl 2-propoxycinnamate

Product 1

HCID 229900333-(2-Propoxyphenyl)-1-propanolYield 96.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To lithium aluminum hydride (6.87 g) suspended in diethyl ether (300 ml) was added dropwise at 0° C. a solution of ethyl 2-propoxycinnamate (21.2 g) in diethyl ether (100 ml) over a period of 40 minutes. After the dropwise addition, the resulting mixture was stirred at room temperature for one hour. Water (7 ml), a 15% aqueous solution of sodium hydroxide (7 ml) and water (21 ml) were added to the reaction mixture, and the resulting mixture was further stirred at room temperature for one hour. The reaction mixture was diluted with diethyl ether and was dried by addition of anhydrous magnesium sulfate. After the resulting mixture was filtered, the filtrate was concentrated under reduced pressure to obtain 3-(2-propoxyphenyl)-1-propanol (17.01 g) as a colorless oil.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe resulting mixture was further stirred at room temperature for one hour
  3. dry with materialwas dried by addition of anhydrous magnesium sulfate
  4. filtrationAfter the resulting mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aa9ca4396b6e4bbb9113ced083fe7323
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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