Sodium Hydroxide → (2-Hydroxyphenyl)acetic acid

HRID 1588404Notes

Reaction equation

HRID 1588404 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[OH-:12].[Na+]>[Cu].O>[OH:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 11970(2-Hydroxyphenyl)acetic acidYield 93%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

`Isopar M` (500 ml), (2-chlorophenyl)acetic acid (51.3 g, 0.3M), copper II sulphate hexahydrate (2.88 g, 10 mM) and sodium hydroxide pellets (84 g, 2.1M) were changed to a 1.5 litre hastalloy vessel equipped with a stirrer and condenser. The temperature of the vessel was increased from ambient using an oil bath, while stirring the reaction mixture. The oil bath was maintained at between 210° C. and 220° C. for 6 hours and then heating was ceased and the vessel was allowed to cool to ambient temperature. Water (500 ml) was added (exothern) and the reaction mixture was stirred for a further 30 minutes. After filtering off some insoluble material (about 600 mg) the phases were separated and the upper organic phase set aside (480-490 ml). The aqueous phase was acidified to pH1 (by test paper) by adding 36% hydrochloric acid (125-155 ml, exothern), and then extracted with isopropyl acetate (2×250 ml). The combined isopropyl acetate extracts were evaporated at 60° C. and about 20 mm Hg on a rotary evaporator to give (2-hydroxyphenyl)acetic acid as brown solid (44-45 g, purity by gas chromatography 94-99%, yield 93-96%).

Workup

  1. customequipped with a stirrer and condenser
  2. temperatureThe temperature of the vessel was increased from ambient
  3. temperatureThe oil bath was maintained at between 210° C. and 220° C. for 6 hours
  4. temperatureheating
  5. stirringthe reaction mixture was stirred for a further 30 minutes
  6. filtrationAfter filtering off some insoluble material (about 600 mg) the phases
  7. customwere separated
  8. additionby adding 36% hydrochloric acid (125-155 ml, exothern)
  9. extractionextracted with isopropyl acetate (2×250 ml)
  10. customThe combined isopropyl acetate extracts were evaporated at 60° C.
  11. customabout 20 mm Hg on a rotary evaporator

Sources & evidence

ORD record
ord-0da8e1bb5ea54d5da170ea253aa01472
Source dataset
uspto-grants-1993_06
Patent number
US05221772

Reaction notes

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