2,2-Dimethoxypropane → HCID 15279440, compound

HRID 1955993Notes

Reaction equation

HRID 1955993 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([SH:11])[C:3]=1[C:4]([OH:6])=[O:5].CO[C:14](OC)([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[C:4](=[O:6])[O:5][C:14]([CH3:16])([CH3:15])[S:11][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 144382762-Chloro-6-sulfanylbenzoic acid

Product 1

HCID 15279440HCID 15279440, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g (106 mmol) of 2-chloro-6-mercaptobenzoic acid, 26 ml (212 mmol) of 2,2-dimethoxypropane and 2 g of Amberlyst 15 (strongly acidic ion exchange resin) are refluxed in 1 l of toluene for 3 h. 100 ml are then distilled off in the course of 2 h, a further 10 ml of 2,2-dimethoxypropane are added, boiling is continued for a short time, and the mixture is stirred overnight at room temperature, filtered and concentrated in vacuo. Yield: 22.4 g (92%) of oil, 1H-NMR (CDCl3) δ=1.82 (s); 7.18-7.40 (m).

Workup

  1. distillation100 ml are then distilled off in the course of 2 h
  2. additiona further 10 ml of 2,2-dimethoxypropane are added
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6641d2749f74e2b9710eda56efc0a7d
Source dataset
uspto-grants-1998_07
Patent number
US05777118

Reaction notes

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