Hydrochloric Acid → HCID 19765108, compound

HRID 359732Notes

Reaction equation

HRID 359732 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].O.[OH-].[Li+].O.Cl>C(O)C>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([S:16][CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrate2×HCID 20064197HCID 20064197, compound

Product 1

HCID 19765108HCID 19765108, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-[[3,5-bis(1,1-dimethylethyl)-4hydroxyphenyl]thio]propanoate (1.16 g, 3.4 mmole) from Example 5 in absolute ethanol (20ml) was added lithium hydroxide hydrate (0.2g, 4.8 mmole). Water was added until the solution became cloudy and the mixture was then stirred for 20 hours Additional lithium hydroxide hydrate (0.75 g, 17.9 mmole) was added and the mixture was stirred for another two hours. The mixture was poured into 0.5 N hydrochloric acid (75 ml) and extracted with diethyl ether (100 ml in two portions). The ether extract was dried over magnesium sulfate, filtered, and concentrated in vacuo to a solid. Recrystallization from hexane gave the title compound, m.p. 110°-113°.

Workup

  1. additionwas added
  2. extractionextracted with diethyl ether (100 ml in two portions)
  3. extractionThe ether extract
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a solid
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-a4968354a61e4299967a93bf4647e6ff
Source dataset
uspto-grants-1991_03
Patent number
US05002967

Reaction notes

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