Hydrochloric Acid → HCID 14773377, compound

HRID 1722042Notes

Reaction equation

HRID 1722042 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:11]1(=[O:16])[O:15][CH:13]([CH3:14])[CH2:12]1.Cl>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:13]([CH3:14])[CH2:12][C:11]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 18303beta-BUTYROLACTONE

Product 1

HCID 14773377HCID 14773377, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 40 g (1 mol) sodium hydroxide in 400 ml water was added 128.6 g (1 mol) 4-chlorophenol and the reaction was heated at reflux for 15 minutes. To the refluxing solution was added 81.5 g (1 mol) of beta-butyrolactone dropwise over 1 hour. The reaction was cooled to 23° C., acidified with 100 ml concentrated hydrochloric acid and extracted with 2×500 ml diethyl ether. The ether layers were combined and extracted with 5×300 ml saturated aqueous sodium bicarbonate solution. The bicarbonate extracts were combined, acidified by slow dropwise addition of 160 ml concentrated hydrochloric acid and extracted with 250 ml diethyl ether. The latter ether extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give the product as a white solid, 24 g (11%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 15 minutes
  3. extractionextracted with 2×500 ml diethyl ether
  4. extractionextracted with 5×300 ml saturated aqueous sodium bicarbonate solution
  5. additionacidified by slow dropwise addition of 160 ml concentrated hydrochloric acid
  6. extractionextracted with 250 ml diethyl ether
  7. extractionThe latter ether extract
  8. washwas washed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7f41157385745d3be2f8ee819236c82
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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