Hydrochloric Acid → 3-(3-Hydroxypropoxy)-4-methoxybenzoic acid

HRID 1158446Notes

Reaction equation

HRID 1158446 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH2:13][CH2:14][CH2:15][OH:16])[CH:5]=1.Cl>C1COCC1.[OH-].[Na+]>[OH:16][CH2:15][CH2:14][CH2:13][O:12][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH3:11])[C:3]([OH:17])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 686170883-(3-Hydroxy-propoxy)-4-methoxy-benzoic acid methyl ester

Product 1

HCID 595125423-(3-Hydroxypropoxy)-4-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3-hydroxy-propoxy)-4-methoxy-benzoic acid methyl ester (1.00 g, 4.16 mmol) in THF (3.0 mL) and 2N NaOH (3.1 mL) is stirred at room temperature over 6 hrs. The mixture is adjusted to pH 1 by addition of 2N aqueous HCl to afford a white suspension. The precipitate is filtered, washed with water and dried in vacuo at 50° C. to give the title compound as white solid. MS: 225.0 [M−H]+. 1H-NMR (CDCl3): δ 1.88 (m, 2H), 3.57 (m, 2H), 3.83 (s, 3H), 4.07 (m, 2H), 4.56 (s, br, 1H), 7.06 (dd, 1H), 7.46 (d, 1H), 7.57 (dd, 1H), 12.7 (s, br, 1H) ppm.

Workup

  1. customto afford a white suspension
  2. filtrationThe precipitate is filtered
  3. washwashed with water
  4. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-e9b2b5752fdc4d4a9b0034b047e91a4d
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…