Hydrochloric Acid → 4'-Methoxycarbonyloxy-4-biphenylcarboxylic acid

HRID 1250326Notes

Reaction equation

HRID 1250326 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[OH-].[Na+].Cl>O>[CH3:5][O:4][C:2]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 183284084'-Methoxycarbonyloxy-4-biphenylcarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl chloroformate (12.90 g, 0.137 mol) was added dropwise, over 10 minutes, to a stirred, cooled (5° C.) solution of compound 3 (10.00 g, 0.047 mol) in sodium hydroxide (5.44 g, 0.136 mol) and water (150 ml). During the addition a white precipitate was formed and this stirred mixture was allowed to warm to room temperature overnight. The resultant mixture was carefully acidified (pH 5) with dilute hydrochloric acid and the resultant voluminous white solid was filtered off, washed with water until acid-free and dried (phosphorus pentoxide) in vacuo.

Workup

  1. additionDuring the addition a white precipitate
  2. customwas formed
  3. filtrationthe resultant voluminous white solid was filtered off
  4. washwashed with water until acid-free and
  5. dry with materialdried (phosphorus pentoxide) in vacuo

Sources & evidence

ORD record
ord-97a2cd869ce24069a9e0c42a5805e4fc
Source dataset
uspto-grants-2002_01
Patent number
US06337420B1

Reaction notes

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