Hydrochloric Acid → HCID 18000594, compound

HRID 478127Notes

Reaction equation

HRID 478127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:25])[C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]([O:7]C)=[O:6].[OH-].[K+].Cl>CO.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:25])[C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18000593HCID 18000593, compound

Product 1

HCID 18000594HCID 18000594, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3,5-dichloro-4-dodecyloxybenzoate, (˜0.78 mol, as above) was dissolved in methanol (1000 mL) and THF (500 mL). 85%-Potassium hydroxide (100 g, 1.52 mol) was dissolved in water (200 mL) and added to the solution. The starting material oiled out, but on gentle heating dissolution was achieved. After stirring at room temperature for 15 minutes the solution was poured into ice cold 2N-HCl with good stirring whereupon the product precipitated out. The white solid was filter off, washed well with water, and air-dried to remove as much of the water as possible. The solid was then suspended in acetonitrile (˜1000 mL) and stirred mechanically for about 1 hr. The solid was then filtered off washed with acetonitrile and air-dried. Yield, 290.6 g.

Workup

  1. additionadded to the solution
  2. temperatureon gentle heating
  3. dissolutiondissolution
  4. stirringwith good stirring whereupon the product
  5. customprecipitated out
  6. filtrationThe white solid was filter off
  7. washwashed well with water
  8. customair-dried
  9. customto remove as much of the water as possible
  10. stirringstirred mechanically for about 1 hr
  11. filtrationThe solid was then filtered off
  12. washwashed with acetonitrile
  13. customair-dried
  14. customYield

Sources & evidence

ORD record
ord-58841a9f078d4919bc1b3a94f8f0b0fe
Source dataset
uspto-grants-2003_11
Patent number
US06641990B1

Reaction notes

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