Methanethiol → HCID 21897297, compound

HRID 488057Notes

Reaction equation

HRID 488057 reaction equation
[OH-].[Na+].[CH3:3][SH:4].[Na].CS.Cl[C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:11][C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[CH:3]=[S:4]

Participants

7

Reactant 4

HCID 878MethanethiolHCID 69962-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 45051789Methylmercaptan sodium

Product 1

HCID 21897297HCID 21897297, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A four-necked flask of 200 ml capacity, equipped with a stirrer, thermometer and reflux condensor, was charged with 11.2 g (0.28 mol) of sodium hydroxide and 80 g of water under a nitrogen atmosphere and 13.5 g (0.28 mol) of methanethiol was bubbled through the charge at room temperature for about 1 hour to prepare an aqueous solution of methanethiol sodium salt. To this aqueous solution was added 28.1 g (0.2 mol) of 2-chlorobenzaldehyde and the reaction was conducted in the presence of 1.1 g of tetra-n-butylammonium bromide (phase transfer catalyst) at 80° C. for 4 hours. The reaction mixture was then cooled to room temperature and extracted with methylene chloride. The methylene chloride layer was separated, concentrated and distilled under reduced pressure to give 28.9 g of 2-methylthiobenzaldehyde (b.p. 116°-118° C./5 mmHg). The yield based on 2-chlorobenzaldehyde was 95%.

Workup

  1. customA four-necked flask of 200 ml capacity, equipped with a stirrer
  2. temperaturethermometer and reflux condensor
  3. additioncharge at room temperature for about 1 hour
  4. extractionextracted with methylene chloride
  5. customThe methylene chloride layer was separated
  6. concentrationconcentrated
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-0e1cbe4aaf7040098ea8759ebbdca197
Source dataset
uspto-grants-1994_03
Patent number
US05298630

Reaction notes

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