Water → 2-Methyl-2-(4-nitrophenyl)propan-1-ol

HRID 1508149Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]([CH3:21])([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[CH3:11].O.[OH-].[Na+]>C1COCC1>[CH3:21][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)([CH3:11])[CH2:9][OH:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (1.00 g, 26.3 mmol) in 50 mL of THF at 0° C. was added 2-methyl-2-(4-nitro-phenyl)-propionic acid methyl ester (2.20 g, 9.86 mmol, Hartwig, et al, J. Am. Chem. Soc, 2004, 126, 5182) in 10 mL of THF dropwise. The resulting mixture was stirred at 0° C. for 3 h and treated with 1 mL of H2O followed by 1 mL of 15% aq NaOH and 3 mL of H2O. The solid was removed by filtration on Celite and the filtrate was concentrated in vacuo to give a light yellow oil (1.56 g, 81%). The product was used in the next step without further purification. 1H-NMR (CDCl3; 400 MHz): δ 7.92 (d, 2H, J=8.6 Hz), 7.55 (d, 2H, J=8.6 Hz), 3.69 (s, 2H), 1.40 (s, 6H).

Workup

customThe solid was removed by filtration on Celite
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-d1fba2793f584a35afa6feeb909c5e1f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221797B2

Reaction notes

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