Hydrochloric Acid → HCID 15749966, compound

HRID 1722043Notes

Reaction equation

HRID 1722043 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[F:10].[C:12]1(=[O:17])[O:16][CH:14]([CH3:15])[CH2:13]1.Cl>O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[F:10])[O:11][CH:14]([CH3:15])[CH2:13][C:12]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18303beta-BUTYROLACTONEHCID 757903-Chloro-4-fluorophenol

Product 1

HCID 15749966HCID 15749966, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 27.2 g (0.68 mol) sodium hydroxide in 272 ml water was added 100 g (0.68 mol) 3-chloro-4-fluorophenol. The solution was warmed to reflux and 55.4 ml (0.68 mol) of beta-butyrolactone was added dropwise over a 1 hour period. The reaction was cooled to 23° C. and the pH brought to 7 with concentrated hydrochloric acid. The neutral solution was washed with 3×150 ml diethyl ether to remove unreacted phenol and then acidified to pH 2 with concentrated hydrochloric acid, extracted with 150 ml 1,2-dichloroethane, dried over magnesium sulfate and concentrated in vacuo to 4.3 g of an oil which by nuclear magnetic resonance examination was composed of 44 mol percent product and 56% 3-hydroxybutyric acid. The original diethyl ether washes were extracted with 3×150 ml saturated sodium bicarbonate. The combined bicarbonate solutions were extracted with 150 ml diethyl ether and then the pH was brought to 2 with concentrated hydrochloric acid. Extraction with diethyl ether, washing with brine and drying over magnesium sulfate and concentration in vacuo gave 16.2 g (10.2%) of title product as an oil.

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux
  3. washThe neutral solution was washed with 3×150 ml diethyl ether
  4. customto remove unreacted phenol
  5. extractionextracted with 150 ml 1,2-dichloroethane
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo to 4.3 g of an oil which by nuclear magnetic resonance examination
  8. extractionThe original diethyl ether washes were extracted with 3×150 ml saturated sodium bicarbonate
  9. extractionThe combined bicarbonate solutions were extracted with 150 ml diethyl ether
  10. extractionExtraction with diethyl ether
  11. washwashing with brine
  12. dry with materialdrying over magnesium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-09087b691a694f32bde5ce28614ef92a
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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