Hydrochloric Acid → HCID 18000593, compound

HRID 478126Notes

Reaction equation

HRID 478126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[O:12][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 89191-BromododecaneHCID 11430Potassium Carbonate2×HCID 76856Methyl 3,5-dichloro-4-hydroxybenzoate

Product 1

HCID 18000593HCID 18000593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3,5-dichloro-4-hydroxybenzoate, (173, 0.78 mol), 1-bromododecane (234 g, 0.94 mol) and potassium carbonate (130 g, 0.94 g) in DMF (1000 mL) were heated to 70° C. with good stirring for about 8 hrs. The reaction was cooled and treated with 2N-HCl to neutralize the excess potassium carbonate. The mixture was then extracted with ethyl acetate. The ethyl acetate was washed with 2N-HCl(×3), dried (MgSO4), filtered and concentrated to give an oil. This oil was taken on to the next step without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washThe ethyl acetate was washed with 2N-HCl(×3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customThis oil was taken on to the next step without further purification

Sources & evidence

ORD record
ord-2787f20038b040bba6c9ccfcee8ede68
Source dataset
uspto-grants-2003_11
Patent number
US06641990B1

Reaction notes

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