Sulfuric Acid → HCID 54286808, compound

HRID 581987Notes

Reaction equation

HRID 581987 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[Br:23])[O:6][CH:7]([C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].S(=O)(=O)(O)O>>[Br:23][C:22]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[O:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]=2[CH:21]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 53906065HCID 53906065, compound

Product 1

HCID 54286808HCID 54286808, compoundYield 44.3%

Procedure

Diethyl 3-methoxy-4-bromophenoxyoxalacetate (D10) (7.8 g, 20 mmoles) was stirred with concentrated sulphuric acid (50 ml) for 30 mins. The mixture was then poured into ice water (500 ml) and extracted with diethyl ether (250 ml). The organics were washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and evaporated to dryness. Flash chromatography on TLC silica gel eluting with dichloromethane gave the title compound (D11) (3.29 g, 44%)

Workup

  1. extractionextracted with diethyl ether (250 ml)
  2. washThe organics were washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d6c441bc055847eaa98ec03e3eb7b283
Source dataset
uspto-grants-1999_07
Patent number
US05922733

Reaction notes

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