Hydrochloric Acid → HCID 86619594, compound

HRID 2236789Notes

Reaction equation

HRID 2236789 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:15][CH2:16][CH2:17][CH3:18])=[C:7]([CH:14]=1)[C:8]([O:10]CCC)=[O:9])=[O:2].[OH-].[Na+].Cl>O1CCCC1.CO.O>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:15][CH2:16][CH2:17][CH3:18])=[C:7]([CH:14]=1)[C:8]([OH:10])=[O:9])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57575421HCID 57575421, compound

Product 1

HCID 86619594HCID 86619594, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of propyl 5-formyl-2-propoxybenzoate (1.0 g, 4.0 mmol) in tetrahydrofuran/methanol/water (20 mL: 20 mL: 8 mL) is added 5 N sodium hydroxide solution (2 mL, 10 mmol). The mixture is heated in a 70° C. oil bath for three hours and then allowed to cool to room temperature. While acidifying to pH 1 with concentrated hydrochloric acid, a white solid precipitated, which is collected and discarded. The filtrate is concentrated under reduced pressure, and the solid residue is collected by filtration and washed with water to give 5-formyl-2-propoxybenzoic acid as flocculent white needles (0.79 g, 95%).

Workup

  1. temperatureto cool to room temperature
  2. customa white solid precipitated
  3. customwhich is collected
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. filtrationthe solid residue is collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-ed86ee8c367b44cf86d93bdef06803ab
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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