Butyl bromide → HCID 22420398, compound

HRID 1720163Notes

Reaction equation

HRID 1720163 reaction equation
[OH:1][C:2]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][CH3:31]>CC(C)=O.O>[CH2:28]([O:1][C:2]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])=[O:5])[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 22420389HCID 22420389, compound

Product 1

HCID 22420398HCID 22420398, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(2-hydroxy-4-methoxybenzoyl)benzoic acid (1 g) and anhydrous potassium carbonate (1.12 g) is heated under reflux in acetone (30 ml) for 30 minutes. Then, 1-bromobutane (1.1 g) is added and the resulting mixture heated under reflux for 48 hours. The reaction mixture is then cooled to room temperature, diluted with water (100 ml) and extracted with ether (3×30 ml). The ether extracts are dried over magnesium sulfate, filtered and evaporated to dryness. The residue is heated under reflux with 2N sodium hydroxide (2 ml) for 4 hours. The mixture is then acidified with concentrated hydrochloric acid, diluted with water (50 ml) and extracted with ether (3×25 ml). Ether extracts are dried over magnesium sulfate, filtered, and evaporated to dryness. The residue is recrystallized from aqueous ethanol to yield 3-(2-butoxy-4methoxybenzoyl)benzoic acid (0.5 g), m.p. 112°-115° C.

Workup

  1. temperatureis heated
  2. temperaturethe resulting mixture heated
  3. temperatureunder reflux for 48 hours
  4. extractionextracted with ether (3×30 ml)
  5. dry with materialThe ether extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. temperatureThe residue is heated
  9. temperatureunder reflux with 2N sodium hydroxide (2 ml) for 4 hours
  10. additiondiluted with water (50 ml)
  11. extractionextracted with ether (3×25 ml)
  12. dry with materialEther extracts are dried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated to dryness
  15. customThe residue is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-da992790ceba49659f1fda6136869c7e
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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