4-Hydroxybenzoic Acid → HCID 14297704, compound

HRID 1728511Notes

Reaction equation

HRID 1728511 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].[F:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15]Br.Cl>C(O)C.O>[F:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 14297708HCID 14297708, compound

Product 1

HCID 14297704HCID 14297704, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

Into a 100 ml-round bottomed flask, 1.52 g (11 mW) of p-hydroxybenzoic acid in 20 ml of ethanol was added. Thereto, 1.45 g (26 mM) of potassium hydroxide in 5 ml of water was added, and 2.15 g (10 mM) of 2-fluorooctyl bromide in 2 ml of ethanol was added, followed by 25 hours of heat refluxing. Thereafter, a solution of 1.45 g (26 mM) of potassium hydroxide in 3 ml of water was added, followed by 5 hours of heat refluxing. After the completion of the reaction, the system was cooled with ice and neutralized with conc. HCl to precipitate a crystal. The crystal was filtered out, and washed with 50 ml of water to recover 1.00 g (yield: 37%) of p-2-fluorooctyloxybenzoic acid.

Workup

  1. temperatureof heat
  2. temperaturerefluxing
  3. waitfollowed by 5 hours
  4. temperatureof heat
  5. temperaturerefluxing
  6. customAfter the completion of the reaction
  7. customto precipitate a crystal
  8. filtrationThe crystal was filtered out
  9. washwashed with 50 ml of water

Sources & evidence

ORD record
ord-6e876278ec0e40aeb1462c7e56f479b2
Source dataset
uspto-grants-1994_07
Patent number
US05328639

Reaction notes

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