Sodium Hydroxide → 6-Bromo-2-hydroxy-3-methoxybenzaldehyde

HRID 2290915Notes

Reaction equation

HRID 2290915 reaction equation
C(=O)([O-])OC[C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([Br:12])[C:5]=1[CH:13]=[O:14].[OH-:17].[Na+]>CO>[Br:12][C:6]1[C:5]([CH:13]=[O:14])=[C:4]([OH:17])[C:9]([O:10][CH3:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 867410853-Bromo-2-formyl-6-methoxyphenylmethyl carbonate

Product 1

HCID 2622376-Bromo-2-hydroxy-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-bromo-2-formyl-6-methoxyphenylmethyl carbonate (100 g, 0.34 mole), 500 mL 10% aqueous NaOH, and 2 L MeOH was stirred at reflux for 2 hours. After cooling to room temperature, the MeOH was removed (in-vacuo). The aqueous solution was cooled to 0° and acidified with concentrated HCl. The solid was filtered, washed with water, and dried (in-vacuo) to yield 107 g yellow solid which was recrystallized from 2-propanol to yield 62 g yellow solid; mp 95°-6°; M+ 230.

Workup

  1. temperatureat reflux for 2 hours
  2. customthe MeOH was removed (in-vacuo)
  3. temperatureThe aqueous solution was cooled to 0°
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried (in-vacuo)

Sources & evidence

ORD record
ord-766b8238e06e4821938af067097686de
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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