Hydrochloric Acid → HCID 68690484, compound

HRID 2246837Notes

Reaction equation

HRID 2246837 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])=[C:7]([CH3:19])[CH:6]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1>[CH3:19][C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68688462HCID 68688462, compound

Product 1

HCID 68690484HCID 68690484, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2,2′,6′-trimethyl-biphenyl-4-carboxylic acid methyl ester of Step A (18.5 g, 75.4 mmole) in tetrahydrofuran was treated with 1 N sodium hydroxide (250 mL) and heated at 90° C. for 20 hours. The mixture was acidified to pH ˜1 with concentrated hydrochloric acid, extracted with dichloromethane, dried over anhydrous magnesium sulfate, and concentrated to give the title compound as a white powder (15.63 g). Recrystallization from aqueous ethanol provided white plates, m.p. 172-173° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-39ebc9013a684d3498f326184e4eb8c1
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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