2-Methyl-4-nitrobenzaldehyde → 1-(2-Methyl-4-nitro-phenyl)ethanol

HRID 1053691Notes

Reaction equation

HRID 1053691 reaction equation
[CH3:1][Li].[CH3:3][C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]>C(OCC)C.[Ti](Cl)(Cl)(Cl)Cl>[CH3:3][C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[CH:6]([OH:7])[CH3:1]

Participants

5

Reactant 2

HCID 126541462-Methyl-4-nitrobenzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 1182769061-(2-Methyl-4-nitro-phenyl)ethanolYield 90%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Following the General Procedure of Description 8, MeTiCl3 was freshly prepared prior to use from commercial titanium tetrachloride (TiCl4) (4.73 mL, 8.17 g, 43.1 mmol) and methyl lithium (MeLi) (1.6 M in Et2O, 26.9 mL, 43.0 mmol) in anhydrous diethyl ether (Et2O) (230 mL). A solution of 2-methyl-4-nitro-benzaldehyde (7b) (7.11 g, 43.0 mmol) in anhydrous Et2O (200 mL) was added. Aqueous work-up afforded 7.0 g (90% yield) of the target compound (7c) as a yellow solid. The material was of sufficient purity to be used directly in the next step without further isolation and purification procedures. Rf: ˜0.24 (EtOAc/Hxn=1:2 v/v). 1H NMR (300 MHz, CDCl3): δ 8.07 (dd, J=8.7, 2.7 Hz, 1H), 7.99 (d, J=2.4 Hz, 1H), 7.72 (d, J=9.0 Hz, 1H), 5.18 (q, J=6.6 Hz, 1H), 2.42, (s, 3H), 1.92-1.88 (br. m, 1H), 1.47 (d, J=6.3 Hz, 3H) ppm.

Workup

  1. customwas freshly prepared

Sources & evidence

ORD record
ord-ecf01317b1ab4154b09f6bc01d86bdaf
Source dataset
uspto-grants-2016_07
Patent number
US09394236B2

Reaction notes

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