Hydrochloric Acid → 7-[5-(2-n-Propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-4-hydroxy-8-n-propylchroman-2-carboxylic acid

HRID 1285257Notes

Reaction equation

HRID 1285257 reaction equation
[C:1]([CH:6]1[CH2:15][CH:14]([OH:16])[C:13]2[C:8](=[C:9]([CH2:37][CH2:38][CH3:39])[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([OH:33])[C:25]=3[CH2:34][CH2:35][CH3:36])=[CH:11][CH:12]=2)[O:7]1)([O:3]CC)=[O:2].O1CCCC1.[OH-].[Na+].Cl>C(O)C>[CH2:34]([C:25]1[C:26]([OH:33])=[C:27]([C:30](=[O:32])[CH3:31])[CH:28]=[CH:29][C:24]=1[O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:10]1[C:9]([CH2:37][CH2:38][CH3:39])=[C:8]2[C:13]([CH:14]([OH:16])[CH2:15][CH:6]([C:1]([OH:3])=[O:2])[O:7]2)=[CH:12][CH:11]=1)[CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 135378792-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-4-hydroxy-8-n-propylchroman

Product 1

HCID 135378777-[5-(2-n-Propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-4-hydroxy-8-n-propylchroman-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g (2.2 mmole) of the compound of Example 28 dissolved in 20 ml ethanol and 35 ml tetrahydrofuran was saponified with 0.3 g NaOH, the reaction mixture acidified with dilute HCl to pH 3 and extracted with ethyl acetate. The organic phase was washed with water until neutral, then with brine and dried with magnesium sulfate. The crude residue after evaporation of the solvent was triturated with benzene and 0.18 (16%) of the title compound as a white solid, mp 95.5°-97.5° C., separated by filtration. Calc: C, 67.68; H, 7.44; Found: C, 67.56; H, 7.34.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water until neutral, then with brine
  3. dry with materialdried with magnesium sulfate
  4. customThe crude residue after evaporation of the solvent
  5. customwas triturated with benzene and 0.18 (16%) of the title compound as a white solid, mp 95.5°-97.5° C.
  6. customseparated by filtration

Sources & evidence

ORD record
ord-4092d372ca6f4a8faee420ba0dde9a87
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

Loading…