Water → 3-(Benzyloxy)-4-chlorobenzoic acid

HRID 1028428

Reaction equation

HRID 1028428 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:13]([OH:15])=[O:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1418724-Chloro-3-hydroxybenzoic acid

Product 1

HCID 672169913-(Benzyloxy)-4-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.67 ml benzylbromide are added dropwise to 1.73 g 3-hydroxy-4-chloro-benzoic acid and 3.04 g potassium carbonate in 10 ml N,N-dimethylformamide, and the reaction mixture is stirred overnight at ambient temperature. Then the reaction mixture is mixed with water and extracted with ethyl acetate. The combined organic phases are dried on magnesium sulphate and evaporated down. The flask residue is taken up in 5 ml of methanol, combined with 3 ml of 10 M aqueous potassium hydroxide solution and stirred for 4 h at 50° C. gerũhrt. The reddish solution is diluted with water and acidified with 3 N aqueous hydrochloric acid. The precipitate formed is suction filtered, washed with water and dried.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined organic phases are dried on magnesium sulphate
  3. customevaporated down
  4. stirringstirred for 4 h at 50° C. gerũhrt
  5. additionThe reddish solution is diluted with water
  6. customThe precipitate formed
  7. filtrationfiltered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-b482f705a77e45a48813b6dd73e82284
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Linked notes

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