Water → 3-(4-Methylphenyl)propan-1-ol

HRID 2240586Notes

Reaction equation

HRID 2240586 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.O.[OH-].[Na+]>O1CCCC1>[C:9]1([CH3:12])[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][CH2:3][OH:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 9855632Methyl 3-(p-tolyl)propanoate

Product 1

HCID 2218933-(4-Methylphenyl)propan-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.24 g of 3-p-tolyl-propionic acid methyl ester (40ab) prepared by above Step 2 was dissolved in 100 ml of tetrahydrofuran under Ar atmosphere. Then 27 ml of lithium aluminium-hydride was added thereto with stirring for 2 hrs at 0° C. After 3 ml of distilled water, 3 ml of NaOH (1N) and 9 ml of distilled water were added to the reaction mixture sequentially, the mixture was stirred for 30 min and filtered using cellite in glass filter and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:2) as an eluant to give 971 mg of 3-p-tolyl-propane-1-ol (40ac) (yield: 93%).

Workup

  1. additionThen 27 ml of lithium aluminium-hydride was added
  2. stirringthe mixture was stirred for 30 min
  3. filtrationfiltered
  4. filtrationfilter
  5. concentrationconcentrated in vacuo
  6. customThe resultant was purified by Silica gel column chromatography with a solvent mixture
  7. additionmixed with methanol and chloroform (1:2) as an eluant

Sources & evidence

ORD record
ord-1f88bbad23ca4e6aaff598d62f45c8f3
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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