Water → 3-(4-Methylphenyl)propan-1-ol

HRID 2261384

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

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 Argon 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

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

Sources & evidence

ORD record: ord-d2322d1f820e4ed485c22ae60201ab55
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846963B2

Linked notes

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