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

HRID 975294Notes

Reaction equation

HRID 975294 reaction equation
CC1(C)C[O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=2)=N1.Cl.C([OH:25])C>>[OH:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:4]([OH:5])=[O:25])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

Product 1

HCID 153808804'-(Hydroxymethyl)-[1,1'-Biphenyl]-2-Carboxylic AcidYield 81%

Procedure

2.0 g (7.11 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline was dissolved in ethanol (30 ml). 2N hydrochloric acid (10 ml) was added hereto, followed by heating under reflux for 3 hours. After the reaction liquid was cooled and concentrated, a saturated aqueous solution of sodium hydrogencarbonate (100 ml) was added thereto, followed by the extraction with chloroform. After the organic phase was washed with water and dried, it was subjected to vacuum concentration. A 20% aqueous solution of sodium hydroxide (20 ml) and ethanol (20 ml) were added to the residue, followed by heating under reflux for 8 hours. After the reaction liquid was cooled to room temperature and adjusted to pH 6 with hydrochloric acid, it was 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 1.31 g of the title compound (yield 81%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customAfter the reaction liquid
  4. temperaturewas cooled
  5. concentrationconcentrated
  6. additiona saturated aqueous solution of sodium hydrogencarbonate (100 ml) was added
  7. extractionfollowed by the extraction with chloroform
  8. washAfter the organic phase was washed with water
  9. customdried
  10. concentrationit was subjected to vacuum concentration
  11. additionA 20% aqueous solution of sodium hydroxide (20 ml) and ethanol (20 ml) were added to the residue
  12. temperatureby heating
  13. temperatureunder reflux for 8 hours
  14. customAfter the reaction liquid
  15. extractionwas extracted with chloroform
  16. washAfter the organic phase was washed with water
  17. customdried
  18. concentrationit was subjected to vacuum concentration
  19. customThe residue was purified by silica gel column chromatography (a chloroform/methanol system)

Sources & evidence

ORD record
ord-8944863d88dd4b659aa8d3e67ee44506
Source dataset
uspto-grants-1997_03
Patent number
US05608068

Reaction notes

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