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

HRID 890899Notes

Reaction equation

HRID 890899 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+].[I-].[K+].Br[CH2:16][CH2:17][CH2:18][OH:19]>C(O)C.O>[OH:19][CH2:18][CH2:17][CH2:16][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 4875Potassium IodideHCID 123083-Bromo-1-propanolHCID 14797Potassium Hydroxide

Product 1

HCID 134232864-(3-Hydroxypropoxy)benzoic acidYield 75.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-hydroxybenzoic acid (25.0 g, 0.18 mol), potassium hydroxide (27.6 g, 0.49 mol), and potassium iodide (3.0 g, 0.018 mol) in ethanol (75 mL) and water (5 mL) was added dropwise 3-bromopropanol (25.6 g, 0.19 mol). The reaction was allowed to continue for 24 h under reflux. The solid residue was filtered off, and the filtrate was evaporated to dryness. The resultant solid was dissolved in water (200 mL) and then acidified with a 10% HCl solution. The precipitate was filtered for recrystallization from ethanol: water (1:1) to yield 1(26.7 g, 75%). 1H NMR (200 MHz, DMSO-d6): δ 1.85 (quintet, 2H, —CH2—), δ 3.55 (t, 2H, —CH2OAr), δ 4.10 (t, 2H, HOCH2—), δ 6.95 (d, 2H, aromatic ring), δ 7.85 (d, 2H, aromatic ring).

Workup

  1. temperatureunder reflux
  2. filtrationThe solid residue was filtered off
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe resultant solid was dissolved in water (200 mL)
  5. filtrationThe precipitate was filtered for recrystallization from ethanol: water (1:1)

Sources & evidence

ORD record
ord-208807c852d44ca99db23f56c5ec9f5d
Source dataset
uspto-grants-2006_02
Patent number
US07001648B2

Reaction notes

Loading…