Hydrochloric Acid → 5-(3-Methylbutoxy)-2-propylthiophenol

HRID 1606105Notes

Reaction equation

HRID 1606105 reaction equation
CN(C)C(=O)[S:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:8]=[CH:7][C:6]=1[CH2:17][CH2:18][CH3:19].[OH-].[K+].CNC.Cl>O.C(O)COCCO>[CH3:15][CH:14]([CH3:16])[CH2:13][CH2:12][O:11][C:9]1[CH:8]=[CH:7][C:6]([CH2:17][CH2:18][CH3:19])=[C:5]([SH:4])[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 14797Potassium HydroxideHCID 21545974S-5-(3-methylbutoxy)-2-propylphenyl N,N-dimethylthiocarbamate

Product 1

HCID 215459855-(3-Methylbutoxy)-2-propylthiophenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

A solution of 136.1 parts of S-5-(3-methylbutoxy)-2-propylphenyl N,N-dimethylthiocarbamate and 280 parts of potassium hydroxide in 1000 parts of digol was stirred under nitrogen at 120° - 130° for 9 hours, after which no dimethylamine could be detected in the effluent nitrogen. The mixture was cooled, poured into 8000 parts of water and the resulting solution was acidified to pH 1 with hydrochloric acid. The mixture was extracted with ether and the latter was washed with water, dried over magnesium sulphate, filtered and evaporated to dryness to give 95.7 g of the desired product 5-(3-methylbutoxy)-2-propylthiophenol.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ether
  3. washthe latter was washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b1f54d07f00b402ab11bb08dbc9756b0
Source dataset
uspto-grants-1976_04
Patent number
US03952013

Reaction notes

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