Hydrochloric Acid → HCID 22091452, compound

HRID 2229198Notes

Reaction equation

HRID 2229198 reaction equation
[Cl:1][C:2]1[C:13]([O:14][CH2:15][CH2:16][Br:17])=[C:12]([O:18][CH3:19])[CH:11]=[CH:10][C:3]=1[C:4]([O:6]CCBr)=[O:5].[OH-].[Na+].Cl>C(O)C>[Br:17][CH2:16][CH2:15][O:14][C:13]1[C:2]([Cl:1])=[C:3]([CH:10]=[CH:11][C:12]=1[O:18][CH3:19])[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22091440HCID 22091440, compound

Product 1

HCID 22091452HCID 22091452, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of bromoethyl 2-chloro-3-bromoethoxy-4-methoxybenzoate (2.0 g, 4.8 mmol) in ethanol (6 ml) is added 2.5 N aqueous sodium hydroxide (4.8 ml, 12 mmol). The resulting mixture is heated at 50° C. until dissolved plus an additional 10 minutes. The solution is cooled, acidified with 3 N HCl, transferred to a separatory funnel and extracted with ethyl acetate (4×25 ml). The combined organic layers are washed with brine (25 ml), dried over magnesium sulfate and evaporated to obtain 1.4 g (93%) of 3-bromoethoxy-2-chloro-4-methoxybenzoic acid.

Workup

  1. dissolutionuntil dissolved plus an additional 10 minutes
  2. temperatureThe solution is cooled
  3. customtransferred to a separatory funnel
  4. extractionextracted with ethyl acetate (4×25 ml)
  5. washThe combined organic layers are washed with brine (25 ml)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-2f1b2bb4edc44358b2a032ea7b355134
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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