Hydrochloric Acid → 3,5-Dimethyl-4-sulfanylphenol

HRID 1438768

Reaction equation

HRID 1438768 reaction equation
[C:1]1([OH:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[S]Cl.C[S-].[Na+].[OH-].[Na+].C[S:18]SC.Cl>C(COC)OC>[SH:18][C:4]1[C:5]([CH3:7])=[CH:6][C:1]([OH:9])=[CH:2][C:3]=1[CH3:8]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79483,5-DimethylphenolHCID 12232Dimethyl DisulfideHCID 14798Sodium HydroxideHCID 4378561Sodium methanethiolateHCID 15930840CID 15930840

Product 1

HCID 145474593,5-Dimethyl-4-sulfanylphenolYield 93%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

61 grams (0.5 mole) of 3,5-xylenol dissolved in 250 cc glyme was added to 67 grams (0.5 mole) of sulfur monochloride dissolved in 200 cc glyme at room temperature. The temperature rose immediately to about 50° C. After 2 minutes, the reaction mixture was poured into 2400 grams of an aqueous solution of about 227 grams (3.4 moles) of sodium methyl mercaptide and 217 grams (5.4 moles) of sodium hydroxide. The mixture was then heated to its boiling point. After the glyme and dimethyl disulfide had boiled off, the mixture was acidified with concentrated hydrochloric acid to precipitate a pale yellow oil which crystallized rapidly to a colorless solid. A 93% yield of 4-mercapto-3,5-xylenol was obtained.

Workup

  1. customrose immediately to about 50° C
  2. temperatureThe mixture was then heated to its
  3. customto precipitate a pale yellow oil which
  4. customcrystallized rapidly to a colorless solid

Sources & evidence

ORD record
ord-4dcda43804e745e389134870905dc2fa
Source dataset
uspto-grants-1977_11
Patent number
US04056568

Linked notes

Loading…