Hydrochloric Acid → HCID 21997470, compound

HRID 1977310Notes

Reaction equation

HRID 1977310 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[CH3:23][O-:24].[Na+].Cl.S(=O)(=O)(O)O>CO.O>[CH3:23][O:24][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 10942334Sodium MethoxideHCID 21997457HCID 21997457, compound

Product 1

HCID 21997470HCID 21997470, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

A solution of methyl 4-[4-(4-bromobutoxy)phenyl]benzoate (1.40 g) in methanol (14 ml) was treated with 28% sodium methoxide in methanol (14 ml) and the solution was reluxed for 5 hours. After cooling to room temperature, the reaction mixture was poured into cold 1N-hydrochloric acid (110 ml) and the resulting precipitate was collected by filtration, washed thoroughly with water and dried to give a white solid. To a mixture of this solid in methanol (20 ml) was added concentrated sulfuric acid (0.5 ml) and refluxed for 4 hours. After cooling to room temperature, the reaction mixture was poured into cold water and the resulting precipitate was collected by filtration, washed thoroughly with water and dried to give methyl 4-[4-(4-methoxybutoxy)phenyl]benzoate (1.16 g) as a white solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed thoroughly with water
  3. customdried
  4. customto give a white solid
  5. temperaturerefluxed for 4 hours
  6. temperatureAfter cooling to room temperature
  7. filtrationthe resulting precipitate was collected by filtration
  8. washwashed thoroughly with water
  9. customdried

Sources & evidence

ORD record
ord-4c20699affa5453e944ec0a204b7c1b8
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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