Dimethyl oxalate → HCID 54697150, compound

HRID 621789Notes

Reaction equation

HRID 621789 reaction equation
[CH3:1][C:2]([S:8][CH:9](O)[C:10]([O:12][CH3:13])=[O:11])(O)[C:3]([O:5]C)=O.C(OC)(=O)[C:16](OC)=[O:17].[Na]>CO>[OH:17][C:16]1[C:3]([OH:5])=[C:2]([CH3:1])[S:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 11120Dimethyl oxalateHCID 5360545SodiumHCID 21243552HCID 21243552, compound

Product 1

HCID 54697150HCID 54697150, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of dimethyl α-methyl-thiodiglycolate (Solladie-Cavallo, Bull. Soc. Chim. Fr., 437 (1968)) (10.2 g, 53 mmoles) and dimethyl oxalate (9.4 g, 79 mmoles) in methanol (25 mL) is added slowly to a solution of sodium (3.8 g, 165 mmoles) in methanol (35 mL) under argon and maintained at 10°-15° C. with an ice bath. After the addition, the mixture is slowly heated to reflux for 1 hour, then cooled and concentrated under reduced pressure. The precipitate is filtered off, rinsed with ether, air dried, dissolved in water and acidified with 4N hydrochloric acid. The precipitate is filtered off, rinsed with water and dried to afford the product (6.8 g); mp 116°-117° C.

Workup

  1. temperaturemaintained at 10°-15° C. with an ice bath
  2. additionAfter the addition
  3. temperaturethe mixture is slowly heated
  4. temperatureto reflux for 1 hour
  5. temperaturecooled
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe precipitate is filtered off
  8. washrinsed with ether, air
  9. customdried
  10. dissolutiondissolved in water
  11. filtrationThe precipitate is filtered off
  12. washrinsed with water
  13. customdried

Sources & evidence

ORD record
ord-20da193c41c844249372fdddf20abeaa
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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