Phenol → Methyl 4-[2'-methoxy-5'-nitro-4'-(phenoxymethyl)phenoxy]butanoate

HRID 1352882Notes

Reaction equation

HRID 1352882 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][C:10]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:12]([O:27][CH3:28])[CH:11]=1>CO>[CH3:28][O:27][C:12]1[CH:11]=[C:10]([CH2:9][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 996PhenolHCID 21101447Methyl 4-[4'-(bromomethyl)-2'-methoxy-5'-nitrophenoxy]butanoate

Product 1

HCID 21101446Methyl 4-[2'-methoxy-5'-nitro-4'-(phenoxymethyl)phenoxy]butanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of phenol (130 mg, 138 mmol) and methyl 4-[4′-(bromomethyl)-2′-methoxy-5′-nitrophenoxy] butanoate (7) (500 mg, 138 mmol) in anhydrous methanol (5 cm3) was added KTOBu (186 mg, 166 mmol). The resulting green mixture was stirred at r.t. for 30 mins after which time a white precipitate had formed. The precipitate was filtered and recrystallised from methanol affording the desired compound 9 as a pure white solid (319 mg, 61%). m.p. 96–98° C.; Found C, 61.0; H, 5.8; N, 4.0; C19H21NO7 requires C, 60.8; H, 5.6; N, 3.7%; Rf 0.64 (SiO2, hexane:EtOAc 2:1 v/v); νmax (KBr disc)/cm−1 3000–2800 (m), 1720 (s), 1610, 1580, 1520, 1280, 1220; δH (300 MHz, CDCl3) 2.21 (2H, q, J 6.7 Hz, CH2), 2.57 (2H, t, J 6.7 Hz, CH2), 3.71 (3H, s, OCH3), 3.91 (3H, s, OCH3), 4.14 (2H, t, J 6.7 Hz, CH2), 5.50 (2H, s, CH2), 6.98–7.02 (3H, m, ar), 7.29–7.34 (3H, m, ar), 7.77 (1H, s, ar) ppm; δc (100 MHz, CDCl3) 24.7 (CH2), 30.4 (CH2), 51.7 (OCH3), 56.3 (OCH3), 67.0 (CH2), 68.2 (CH2), 109.4 (CH), 109.6 (CH), 115.0 (CH), 121.5 (CH), 129.6 (CH), 129.7 (CH), 138.9, 147.0, 154.3, 158.1, 173.2 (COOCH3) ppm; m/z (FAB) 376 [(MH+), 20%], 282 [(M-C6H5O), 80%].

Workup

  1. additionwas added KTOBu (186 mg, 166 mmol)
  2. customhad formed
  3. filtrationThe precipitate was filtered
  4. customrecrystallised from methanol affording the desired compound 9 as a pure white solid (319 mg, 61%)

Sources & evidence

ORD record
ord-381acb06826c4e2f8dc3de2b22c4131c
Source dataset
uspto-grants-2007_05
Patent number
US07220784B2

Reaction notes

Loading…