Hydrochloric Acid → HCID 14693075, compound

HRID 326396Notes

Reaction equation

HRID 326396 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[OH:16])[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[C:19](OC(=O)C)(=[O:21])[CH3:20].Cl>O>[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16][C:19](=[O:21])[CH3:20])[C:10]([OH:12])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 115865496-Hydroxy[1,1′-biphenyl]-3-carboxylic acid

Product 1

HCID 14693075HCID 14693075, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-phenyl-4-hydroxybenzoic acid (131.1 g, 0.061 mole) and a 50 weight percent aqueous solution of NaOH (10.5 g, 0.131 mole) in 350 ml of deionized water was added to a 500 ml, three-necked, round-bottom flask equipped with a thermometer and a polytetrafluoroethylene-coated magnetic stir bar. The solution was stirred to homogeneity and then immersed in an ice water bath. With the solution temperature at 10° C., acetic anhydride (12.7 g, 0.124 mole) was added rapidly with stirring. Immediately, a white precipitate began to form. The reaction mixture was stirred for one hour at 10° C., then neutralized with concentrated HCl. The precipitate was filtered, washed in 500 ml of deionized water for one hour, filtered, and dried in an 80° C. vacuum oven for three hours yielding an off-white solid. The solid was recrystallized from a toluene and hexane mixture to give a fluffy white solid, 3-phenyl-4-acetoxybenzoic acid with a m.p. of 185° C. to 187° C.

Workup

  1. customthree-necked, round-bottom flask equipped with a thermometer and a polytetrafluoroethylene-coated magnetic stir bar
  2. customimmersed in an ice water bath
  3. stirringwith stirring
  4. customto form
  5. stirringThe reaction mixture was stirred for one hour at 10° C.
  6. filtrationThe precipitate was filtered
  7. washwashed in 500 ml of deionized water for one hour
  8. filtrationfiltered
  9. customdried in an 80° C. vacuum oven for three hours
  10. customyielding an off-white solid
  11. customThe solid was recrystallized from a toluene and hexane mixture

Sources & evidence

ORD record
ord-d646333144384e0490ed2df99df02e64
Source dataset
uspto-grants-1993_12
Patent number
US05268443

Reaction notes

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