Formaldehyde → 2-(4-Methoxycarbonyl-2-nitrophenyl)propanol

HRID 2357141Notes

Reaction equation

HRID 2357141 reaction equation
CO[C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.[CH2:16]=[O:17].C[C:19](C)([O-:21])C.[K+]>CS(C)=O>[CH3:16][O:17][C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:11])[CH2:19][OH:21])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1)=[O:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 21938352Methyl 4-ethyl-3-nitrobenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 684541792-(4-Methoxycarbonyl-2-nitrophenyl)propanolYield 38%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 4-ethyl-3-nitrobenzoic acid methyl ester (11d) (10 g, 48 mmol) and paraformaldehyde (1.8 g, 60 mmol) in DMSO (10 mL) was added in portions potassium tert-butoxide (1.46 g, 12 mmol), during which the colour of the reaction mixture was changing from yellow to purple. After stirring for 2.5 hours at room temperature, the reaction mixture was directly applied to the silica gel bed of a chromatography column (100 g silica, 3.5×14 cm) and eluted with hexane/ethyl acetate (EA) (3:1, v/v). The slightly yellow product (4d) was obtained in 38% yield (4.42 g, 18 mmol). Rf=0.24 (hexanes/EtOAc 7:3). 1H NMR (250 MHz, CDCl3) δ 8.36 (d, 1H, arom. H(3)), 8.18 (dd, 1H, arom. H(5)), 7.58 (d, 1H, arom. H(6)), 3.93 (s, 3H, COOCH3), 3.78 (m, 2H, α-CH2), 3.54 (sextet, 1H, β-CH), 1.69 (d, 3H, CH3).

Workup

  1. washeluted with hexane/ethyl acetate (EA) (3:1

Sources & evidence

ORD record
ord-d0615736ac9f47c38178b868218079ba
Source dataset
uspto-grants-2010_07
Patent number
US07759513B2

Reaction notes

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