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

HRID 1285245Notes

Reaction equation

HRID 1285245 reaction equation
[C:1]([CH:6]1[CH2:15][C:14](=[O: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].[OH-].[Na+]>C(O)C.O1CCCC1>[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]([C:14](=[O:16])[CH2:15][CH:6]([C:1]([OH:3])=[O:2])[O:7]2)=[CH:12][CH:11]=1)[CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 202504682-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchroman-4-one

Product 1

HCID 202504547-[5-(2-n-Propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchroman-4-one-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
5 °C

Procedure

1.35 g (2.5 mmole) of the compound of Example 3 was dissolved in 50 ml of 50% ethanol-tetrahydrofuran in a 250 ml single neck round bottom flask equipped with a magnetic stirring bar. The contents of the flask were cooled to 5° C. in an ice bath and 25 ml of 0.2N sodium hydroxide solution was added. The reaction mixture was stirred at room temperature for eight hours. Most of the solvent was removed by rotoevaporation, 50 ml of water was added and the aqueous mixture acidified with dilute hydrochloric acid. The acidified solution was extracted three times with 150 ml portions of ethyl acetate and the combined extract washed once with brine. The ethyl acetate extract was dried over anhydrous magnesium sulfate, filtered, and the ethyl acetate removed by rotoevaporation to give 1.19 g (93%) of the title compound as a white solid, mp. 166°-168° C. Calc: C, 67.95; H, 7.08, Found: C, 67.79; H, 7.04.

Workup

  1. customequipped with a magnetic stirring bar
  2. customMost of the solvent was removed by rotoevaporation, 50 ml of water
  3. additionwas added
  4. extractionThe acidified solution was extracted three times with 150 ml portions of ethyl acetate
  5. extractionthe combined extract
  6. washwashed once with brine
  7. extractionThe ethyl acetate extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe ethyl acetate removed by rotoevaporation

Sources & evidence

ORD record
ord-1942ff270c0e43d49f6eb7eb2a2ca0c2
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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