Hydrochloric Acid → 2-Hydroxy-3,4,6-trimethylbenzoic acid phenylester

HRID 128000Notes

Reaction equation

HRID 128000 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[C:9]([CH3:12])[CH:8]=[C:7]([CH3:13])[C:3]=1[C:4]([OH:6])=[O:5].[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.P(Cl)(Cl)(Cl)=O.Cl>O.C1(C)C=CC=CC=1>[C:14]1([O:5][C:4](=[O:6])[C:3]2[C:7]([CH3:13])=[CH:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:2]=2[OH:1])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 24813Phosphorus oxychlorideHCID 137651862-Hydroxy-3,4,6-trimethylbenzoic acid

Product 1

HCID 137651872-Hydroxy-3,4,6-trimethylbenzoic acid phenylesterYield 49.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a 500 ml three-necked flask fitted with a mechanical stirrer, a reflux condenser connected to a water pump to absorb the gaseous hydrochloric acid formed during the reaction, and a dropping funnel, were placed 200 ml of dry toluene and 54 g (0.3 mole) of 2-hydroxy-3,4,6-trimethylbenzoic acid prepared in step (1), and 56.4 g (0.6 mole) of phenol were added. The mixture was heated at 100° C. util the reagents were completely dissolved. 27 ml of phosphorous oxychloride were than added dropwise over 30 minutes, and the mixture was refluxed (110° C.) for 8 hours. A substantial evolution of gaseous hydrochloric acid took place. The mixture was cooled to 80° C. and 150 ml of water were added. The aqueous layer was decanted, and the organic layer was washed a second time with an aqueous solution of sodium bicarbonate. The aqueous layer was decanted and the toluene solution was dried with anhydrous magnesium sulfate. The solution was filtered, and the toluene solvent was distilled off. The residue was dissolved in 90 ml of boiling isopropanol and the desired product crystallized upon cooling. 38 g of a white product were obtained (M.P.=74° C.).

Workup

  1. customIn a 500 ml three-necked flask fitted with a mechanical stirrer, a reflux condenser
  2. customto absorb the gaseous hydrochloric acid
  3. customformed during the reaction, and a dropping funnel
  4. additionwere added
  5. dissolutionwere completely dissolved
  6. additionthan added dropwise over 30 minutes
  7. temperaturethe mixture was refluxed (110° C.) for 8 hours
  8. temperatureThe mixture was cooled to 80° C.
  9. customThe aqueous layer was decanted
  10. washthe organic layer was washed a second time with an aqueous solution of sodium bicarbonate
  11. customThe aqueous layer was decanted
  12. dry with materialthe toluene solution was dried with anhydrous magnesium sulfate
  13. filtrationThe solution was filtered
  14. distillationthe toluene solvent was distilled off
  15. dissolutionThe residue was dissolved in 90 ml of boiling isopropanol
  16. customthe desired product crystallized
  17. temperatureupon cooling

Sources & evidence

ORD record
ord-f97ee5024d6b432c9ddb47bc5baef03b
Source dataset
uspto-grants-1981_03
Patent number
US04258120

Reaction notes

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