1,2-Ethanedithiol → 2-(1,3-Dithiolan-2-yl)-phenylacetic acid methyl ester

HRID 1900218Notes

Reaction equation

HRID 1900218 reaction equation
[CH2:1]([SH:4])[CH2:2][SH:3].[CH3:5][O:6][C:7](=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=O.[OH-].[Na+]>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[S:4][CH2:1][CH2:2][S:3]1

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 14798Sodium HydroxideHCID 12241427Methyl 2-(2-formylphenyl)acetate

Product 1

HCID 544394712-(1,3-Dithiolan-2-yl)-phenylacetic acid methyl esterYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

10 ml of 1,2-ethanedithiol (0.12 moles) and 115 ml of trifluoro diboro diethyletherate are added to a solution of 22 g (0.12 moles) of 2-formyl-phenylacetic acid methyl ester in 100 ml of methylene chloride at 20° C. The system is agitated at 20° C. for 48 hours. 152 ml of 5% sodium hydroxide are added, the phases are separated, the organic phase is dried over magnesium sulphate and the solvent is evaporated under vacuum at +30° C. In this manner 29.7 g of 2-(1,3-dithiolan-2-yl)-phenylacetic acid methyl ester are obtained in the form of a yellow liquid. This crude product is saponified without the need for further purification.

Workup

  1. customthe phases are separated
  2. dry with materialthe organic phase is dried over magnesium sulphate
  3. customthe solvent is evaporated under vacuum at +30° C

Sources & evidence

ORD record
ord-63bd59dc0dc941188748b0f11f42354a
Source dataset
uspto-grants-1996_11
Patent number
US05574153

Reaction notes

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