Sodium Hydroxide → HCID 89656061, compound

HRID 626113Notes

Reaction equation

HRID 626113 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][Br:15])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][Br:15])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89656467HCID 89656467, compound

Product 1

HCID 89656061HCID 89656061, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred solution of methyl 3-bromo-4-(2-bromoethoxy)benzoate (4.0 g, 1.0 eq) in MeOH/H2O (v/v 2:1, 60 mL) was added NaOH (0.715 g, 1.5 eq). The mixture was then refluxed for 25 min, and concentrated under reduced pressure. The residue was poured into water and washed with EtOAc. To the aqueous layer was added 3 N HCl to give the desired product as a white solid (3.4 g, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.07 (s, 1H), 7.92 (d, J=8.4 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 4.50 (t, J=5.6 Hz, 2H), 3.85 (t, J=5.6 Hz, 2H)

Workup

  1. temperatureThe mixture was then refluxed for 25 min
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was poured into water
  4. washwashed with EtOAc
  5. additionTo the aqueous layer was added 3 N HCl

Sources & evidence

ORD record
ord-b017cf7a10794376b5726e33e12c70f7
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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