Hydrochloric Acid → HCID 15578414, compound

HRID 1659491Notes

Reaction equation

HRID 1659491 reaction equation
[CH3:1][C:2]1([CH2:7][C:8](=[O:10])[CH3:9])[O:6][CH2:5][CH2:4][O:3]1.[C:11](OCC)(=O)[C:12](OCC)=[O:13].[O-]CC.[Na+].[Na].Cl>C(O)C.O>[CH3:1][C:2]1[O:6][C:5]([C:4]([O:13][CH2:12][CH3:11])=[O:3])=[CH:9][C:8](=[O:10])[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5600412-Propanone, 1-(2-methyl-1,3-dioxolan-2-yl)-HCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 15578414HCID 15578414, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2-methyl-2-(2-oxopropyl)-1,3-dioxolane (49 g) and diethyl oxalate (55 ml) in ethanol (50 ml) was added over 30 minutes to a stirred, cooled, solution of sodium ethoxide prepared by dissolving sodium (9.4 g) in ethanol (150 ml). The solution was stirred for 5 hours at room temperature and then acidified with 5 M hydrochloric acid (200 ml) and then stirred for a further hour. The mixture was diluted with water (800 ml) and extracted with ethyl acetate, the extract was dried and evaporated and the residue was distilled under vacuum (bp 110°-120° C./0.2 mm). The distillate (53.8 g) was crystallised from ether-petroleum ether 40°-60° C. to give ethyl 6-methyl-4-oxo-4H-pyran-2-carboxylate (mp 35°-38° C.).

Workup

  1. temperaturecooled
  2. stirringstirred for a further hour
  3. extractionextracted with ethyl acetate
  4. customthe extract was dried
  5. customevaporated
  6. distillationthe residue was distilled under vacuum (bp 110°-120° C./0.2 mm)
  7. customThe distillate (53.8 g) was crystallised from ether-petroleum ether 40°-60° C.

Sources & evidence

ORD record
ord-6c0158c9afa44bd38de749bb4cc9a362
Source dataset
uspto-grants-1981_12
Patent number
US04304728

Reaction notes

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