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

HRID 533492Notes

Reaction equation

HRID 533492 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-3b6fca4ed7794a7d874e9c96bfc12c39
Source dataset
uspto-grants-2014_10
Patent number
US08853270B2

Reaction notes

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