Hydrochloric Acid → HCID 54283915, compound

HRID 1459447Notes

Reaction equation

HRID 1459447 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([OH:15])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12])[CH2:2][CH2:3][CH3:4].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>C(O)C.O>[CH2:16]([O:15][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 9815700Benzoic acid, 5-butoxy-2-hydroxy-

Product 1

HCID 54283915HCID 54283915, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Procedure

A suspension containing 1.9 g (9 mmol) of 5-butoxy-2-hydroxybenzoic acid, 3.85 g (30 mmol) of benzyl chloride and 5 g (36 mmol) of anhydrous potassium carbonate in 18 ml of anhydrous ethanol was boiled under reflux for 20 hours while stirring. The reaction mixture was cooled to room temperature and after adding 20 ml of water and thoroughly shaking, the three phases formed were separated. The medium phase was boiled under reflux with 1.1 g (27.5 mmol) of sodium hydroxide dissolved in 7 ml of ethanol and 5 ml of water for 2.5 hours under stirring. After cooling down the solution was mixed with 15 ml of water under cooling by ice, the pH value of the mixture was adjusted to 4 by adding 5M hydrochloric acid and stirred for 1 hour. After extracting the product with ethyl acetate and drying, the solution was evaporated to dryness under reduced pressure to give 1.5 g (55%) ot the aimed product, m.p.: 79°-82° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. stirringthoroughly shaking
  3. customthe three phases formed
  4. customwere separated
  5. temperatureAfter cooling down the solution
  6. temperatureunder cooling by ice
  7. stirringstirred for 1 hour
  8. extractionAfter extracting the product with ethyl acetate
  9. customdrying
  10. customthe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-38d975eab5a14de7a55907048ddf3577
Source dataset
uspto-grants-1998_12
Patent number
US05854250

Reaction notes

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