Sodium Hydroxide → 22-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid

HRID 2412846Notes

Reaction equation

HRID 2412846 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36]C)=[O:35].[OH-].[Na+]>CO>[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12824096HCID 12824096, compound

Product 1

HCID 1282407422-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 15 ml of methanol is dissolved 300 mg of methyl 22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoate followed by addition of 20 ml of a 14% aqueous solution of sodium hydroxide. The mixture is stirred at 50°-60° C. for 1.5 hours. The reaction mixture is made acidic with 3N--HCl and extracted with ethyl acetate. The extract is washed with water and, after drying, the solvent is distilled off under reduced pressure. The residue is recrystallized from methanol to obtain 22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid (IV:n=21), m.p. 67° C.-68° C. NMR(δ, in deuteriochloroform): 1.27(38H,b,CH2), 2.24(3H,s,nuclear CH3), 2.28-2.56(4H,m,CH2COO, nuclear CH2), 3.80(3H,s,OCH3), 3.84(3H,s,OCH3), 6.24(1H,s, nuclear H)

Workup

  1. extractionHCl and extracted with ethyl acetate
  2. washThe extract is washed with water
  3. customafter drying
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-9fdae08b440143c3ab3bdc4481e978e2
Source dataset
uspto-grants-1985_01
Patent number
US04495104

Reaction notes

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