2-Chloro-1,1-diethoxyethane → 1-[(2,2-Diethoxyethyl)sulfanyl]-4-methylbenzene

HRID 437585Notes

Reaction equation

HRID 437585 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Cl)[CH3:2].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.[Na]>CC(N(C)C)=O>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][S:17][C:14]1[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=1)[CH3:2]

Participants

4

Reactant 2

HCID 121282-Chloro-1,1-diethoxyethaneHCID 6688669910486-08-5

Product 1

HCID 70153171-[(2,2-Diethoxyethyl)sulfanyl]-4-methylbenzene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

152.5 Grams (1 mole) of chloroacetaldehyde-diethylacetal were heated at 100° C for 6 hours on the steam bath, together with 162 g (1 mole) of 4-methylthiophenol-sodium salt in 200 ml of dimethylacetamide (in a manner analogous to Comptes Rendus 194, 617 (1932)). After the precipitated sodium chloride had been suction-filtered, the solvent was removed by distillation under reduced pressure. 4-Methylthio-phenoxyacetaldehyde-diethylacetal was obtained as an oily residue which was directly further reacted.

Workup

  1. filtrationAfter the precipitated sodium chloride had been suction-filtered
  2. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0d4a5692a6c04db498fb9f9baba2e154
Source dataset
uspto-grants-1977_06
Patent number
US04031232

Reaction notes

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