4-Hydroxybenzoic Acid → 4-(3-Hydroxypropoxy)benzoic acid

HRID 55919Notes

Reaction equation

HRID 55919 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.Br[CH:14]([OH:17])[CH2:15][CH3:16]>CCO>[OH:17][CH2:14][CH2:15][CH2:16][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 14798Sodium HydroxideHCID 12887879Bromopropanol

Product 1

HCID 134232864-(3-Hydroxypropoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An aqueous solution of NaOH (1 mol) and KI (0.05 mmol) was added to a solution of 4-hydroxybenzoic acid (0.5 mmol) and 400 mL EtOH solution under a nitrogen atmosphere and stirred. After stirring for 30 minutes, an EtOH solution including bromopropanol (0.55 mmol) was dropped thereinto, and then, reacted for 24 hours after elevating to 80° C. A solvent was removed from a reaction product and hydrochloric acid-treatment was carried out. A solid phase was isolated through filteration, and 4-(3-hydroxypropoxy)benzoic acid as a compound of Formula 4 was synthesized.

Workup

  1. stirringAfter stirring for 30 minutes
  2. additionwas dropped
  3. customreacted for 24 hours
  4. customafter elevating to 80° C
  5. customA solvent was removed from a reaction product and hydrochloric acid-treatment

Sources & evidence

ORD record
ord-eccf99f572274037baf1114c2e33265b
Source dataset
uspto-grants-2016_09
Patent number
US09434682B2

Reaction notes

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