Sodium sulfate decahydrate → (2'-Methyl-6'-propylbiphenyl-3-yl)methanol

HRID 2422273Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH3:10])[C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](OC)=[O:18])[CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH3:10])[C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution (6.3 mL) of methyl 2′-methyl-6′-propylbiphenyl-3-carboxylate (0.63 g, 2.35 mmol) in tetrahydrofuran was added lithium aluminum hydride (0.089 g, 2.35 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 2 hrs. Sodium sulfate 10 hydrate (1.5 g, 4.7 mmol) was gradually added to the reaction mixture, and the mixture was stirred at room temperature for 5 hrs. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give the title compound (0.50 g, yield 88%) as a colorless oil.

Workup

stirringthe mixture was stirred at the same temperature for 2 hrs
stirringthe mixture was stirred at room temperature for 5 hrs
filtrationThe insoluble material was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

Sources & evidence

ORD record: ord-958b5b313fa248fd91cf33dbfa665c99
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960369B2

Reaction notes

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