Sulfuric Acid → 4'-(Hydroxymethyl)-[1,1'-Biphenyl]-2-Carboxylic Acid

HRID 975295Notes

Reaction equation

HRID 975295 reaction equation
S(=O)(=O)(O)O.CC1(C)C[O:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=2)=N1.[OH-:27].[Na+]>O>[OH:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:9]([OH:10])=[O:27])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

Product 1

HCID 153808804'-(Hydroxymethyl)-[1,1'-Biphenyl]-2-Carboxylic AcidYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Water (6 ml) and sulfuric acid (3.6 g) were added to 2.0 g (7.11 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline, followed by heating under reflux for 30 hours. After the reaction liquid was cooled, it was neutralized with a 10% aqueous solution of sodium hydroxide and extracted with chloroform. After the organic phase was washed with water and dried, it was subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a chloroform/methanol system) to give 1.05 g of the title compound (yield 65%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 30 hours
  3. customAfter the reaction liquid
  4. temperaturewas cooled
  5. extractionextracted with chloroform
  6. washAfter the organic phase was washed with water
  7. customdried
  8. concentrationit was subjected to vacuum concentration
  9. customThe residue was purified by silica gel column chromatography (a chloroform/methanol system)

Sources & evidence

ORD record
ord-7144b61287984bf88077d3424884bc97
Source dataset
uspto-grants-1997_03
Patent number
US05608068

Reaction notes

Loading…