Ethyl homovanillate → Homovanillic Acid

HRID 2170757Notes

Reaction equation

HRID 2170757 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1)C>CO.O>[OH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:15])=[O:3])=[CH:7][C:8]=1[O:13][CH3:14]

Participants

4

Reactant 1

HCID 108965Ethyl homovanillate

Product 1

HCID 1738Homovanillic AcidYield 96.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester (2 g, 9.51 mmol) and LiOH monohydrate (1.2 g, 28.5 mmol) in MeOH (20 ml) and water (10 ml) was stirred at RT for 14 h. The reaction mixture was concentrated under vacuum, diluted into water and neutralized by the addition of HCl 2 M in water (14.3 ml). The resulting slurry was extracted with DCM (3×) and AcOEt (2×) and the combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (1.67 g, 9.17 mmol, 96%) as a brownish solid, which was used in the next step without further purification. HPLC: AtRet=0.77 min; LC-MS: m/z 183.4 [M+H]+; NMR (400 MHz, DMSO-d6): 3.43 (s, 2H), 3.74 (s, 3H), 6.61-6.66 (m, J=8.1, 2.0, 1H), 6.67-6.72 (m, 1H), 6.81 (d, J=2.0, 1H), 8.81 (s, 1H), 12.17 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additiondiluted into water
  3. additionneutralized by the addition of HCl 2 M in water (14.3 ml)
  4. extractionThe resulting slurry was extracted with DCM (3×) and AcOEt (2×)
  5. dry with materialthe combined organic fractions were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d9c3cf87e83c48458494771132278c1a
Source dataset
uspto-grants-2015_06
Patent number
US09051279B2

Reaction notes

Loading…