Water → 3-[(3,5-Di-tert-butyl-4-hydroxyphenyl)sulfanyl]propanoic acid

HRID 359736Notes

Reaction equation

HRID 359736 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[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>CO>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([S:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 13531084HCID 13531084, compound

Product 1

HCID 150352573-[(3,5-Di-tert-butyl-4-hydroxyphenyl)sulfanyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoate (1.0 g, 3 mmole) was added to a clear solution of lithium hydroxide hydrate (0.64 g, 15 mmole) in methanol (15 ml). Water was added until the solution became cloudy and the mixture was then stirred overnight. The mixture was concentrated to about 10 ml and acidified with cold (5° ) 10% hydrochloric acid. The resultant precipitate was collected by filtration, washed with water, and air dried Recrystallization from cyclohexane gave the title compound, m.p. 108°-110°.

Workup

  1. concentrationThe mixture was concentrated to about 10 ml
  2. customacidified with cold (5° ) 10% hydrochloric acid
  3. filtrationThe resultant precipitate was collected by filtration
  4. washwashed with water, and air
  5. customdried
  6. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-5ef6444245da46d38210c19b03166982
Source dataset
uspto-grants-1991_03
Patent number
US05002967

Reaction notes

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