Lithium Hydroxide → 4-[[[3-(4-Acetyl-3 hydroxy-2-propylphenoxy)propyl]thio]methyl]1,3 oxathiolane-2,2-dipropanoic acid

HRID 1650234Notes

Reaction equation

HRID 1650234 reaction equation
[C:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][CH:14]2[CH2:18][O:17][C:16]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])([CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[S:15]2)=[C:6]([CH2:35][CH2:36][CH3:37])[C:5]=1[OH:38])(=[O:3])[CH3:2].[OH-].[Li+]>C(O)C>[C:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][CH:14]2[CH2:18][O:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[S:15]2)=[C:6]([CH2:35][CH2:36][CH3:37])[C:5]=1[OH:38])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 14405887Diethyl 4-[[[3 (4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]methyl]-1,3 oxathiolane-2,2-dipropanoate

Product 1

HCID 144058884-[[[3-(4-Acetyl-3 hydroxy-2-propylphenoxy)propyl]thio]methyl]1,3 oxathiolane-2,2-dipropanoic acidYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Example 2 (3 g, 0.0052 mol) was dissolved in ethanol (50 ml). Aqueous lithium hydroxide solution (2 M, 9.2 ml) as added and the reaction solution was stirred at room temperature for 3 hrs. Ethanol was removed using the rotary evaporator and the aqueous residue was acidified to pH2 using aqueous 0.5 N sodium bisulfate solution. The oil which separated was extracted with ethyl acetate and the organic layer dried over anhydrous magnesium sulfate. The drying agent was filtered and the filtrate concentrated on the rotary evaporator to give 2.53 g of a colorless oil which was dried at 70° (0.1 mm Hg) for 5 hrs. to give the title compound.

Workup

  1. customEthanol was removed
  2. customthe rotary evaporator
  3. customThe oil which separated
  4. extractionwas extracted with ethyl acetate
  5. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered
  7. concentrationthe filtrate concentrated on the rotary evaporator

Sources & evidence

ORD record
ord-155ec3738751482ab2c5baa144e4dd7b
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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