Hydrochloric Acid → Elsibucol

HRID 434109Notes

Reaction equation

HRID 434109 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][C:17]([S:20][C:21]2[CH:34]=[C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:24]([O:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[C:23]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:22]=2)([CH3:19])[CH3:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].CO.O.O.[OH-].[Li+].Cl>[Cl-].[Na+].O>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([S:16][C:17]([S:20][C:21]2[CH:22]=[C:23]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:24]([O:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:34]=2)([CH3:18])[CH3:19])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 18756961Methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrateHCID 22242641Methanol--water (1/1)

Product 1

HCID 10218732ElsibucolYield 64.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrate (0.95 g, obtained above) was dissolved in THI/MeOH/H2O (4:1;1, 15.4 mL) and lithium hydroxide hydrate (0.19 g) was added. The mixture was stirred at room temperature for four hours and then acidified with 0.3 N HCl. The mixture was poured into brine and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated to give 0.60 g of 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyric acid (Compound A) as a solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-fc3a3ebaabca44a48bf6a2b8f6095652
Source dataset
uspto-grants-2003_12
Patent number
US06670398B2

Reaction notes

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