4-Hydroxybenzoic Acid → HCID 21315467, compound

HRID 236847Notes

Reaction equation

HRID 236847 reaction equation
[Na].[OH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH3:12]N(C)C=O.[CH2:17]([O:21][CH2:22][CH2:23]Br)[CH2:18][CH2:19]C>C1(C)C=CC=CC=1.O>[CH3:12][CH:17]([O:21][CH2:22][CH2:23][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6228DimethylformamideHCID 1387612-Butoxyethyl bromideHCID 5360545Sodium

Product 1

HCID 21315467HCID 21315467, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

To a 1 l three-neck flask were added 70 g of sodium salt of p-hydroxybenzoic acid ##STR4## and 200 ml of N,N-dimethylformamide, and the contents were heated under reflux. To the heated contents, 50 g of β-n-butoxyethyl bromide was dropped over a period of 30 minutes and heating was continued under reflux for further 8 hours. After cooling with water, 300 ml of water and 200 ml of toluene were added to the contents and after shaking, the resulting organic layer was separated, washed with 4 N hydrochloric acid and then with a 20% aqueous solution of sodium hydroxide. After distilling off toluene and heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours, the resulting material was neutralized with hydrochloric acid to precipitate the objective material. After washing with water, the objective material was recrystallized from ethanol to obtain 55 g of p-(β-n-butoxy)ethoxybenzoic acid. The melting point of this material was 114.5°-115° C. and the values of the elemental analysis thereof showed a good agreement with the calculated values as seen below.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. temperatureunder reflux for further 8 hours
  4. additionwere added to the contents
  5. customthe resulting organic layer was separated
  6. washwashed with 4 N hydrochloric acid
  7. distillationAfter distilling off toluene
  8. temperatureheating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours
  9. customto precipitate the objective material
  10. washAfter washing with water
  11. customthe objective material was recrystallized from ethanol

Sources & evidence

ORD record
ord-98caac1e6e284fa59d9afd876a7c5429
Source dataset
uspto-grants-1979_06
Patent number
US04158011

Reaction notes

Loading…