Oxalic Acid → HCID 20269924, compound

HRID 485281Notes

Reaction equation

HRID 485281 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Br)=[CH:5][CH:4]=1.[C:11](O)(=O)[C:12]([OH:14])=[O:13]>C1COCC1>[C:3]([O:13][C:12]([CH2:11][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:11][C:12]([O:14][C:6]([CH3:9])([CH3:7])[CH3:5])=[O:13])=[CH:5][CH:4]=1)=[O:14])([CH3:8])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 693351,4-Bis(bromomethyl)benzene

Product 1

HCID 20269924HCID 20269924, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 200 ml of THF and 44 ml (0.315 mol) of diisopropylamine was added 168 ml (286 mmols) of hexane solution of 1.70 mol dm-3 butyl lithium at 0° C. The mixture was stirred at 0° C. for 10 minutes and then cooled to -78° C. To the mixture was added 35 ml (260 mmols) of t-butyl acetate, followed by stirring for 1 hour. To the lithium enolate thus formed was added 300 ml of THF solution of 26.4 g (0.1 mol) of α,α'-dibromo-p-xylene. The reaction mixture was stirred at -78° C. to room temperature for 12 hours, and 100 ml of saturated aqueous solution of oxalic acid was thereafter added thereto. The organic layer was separated off and subjected to extraction with ether. The organic layer was dried over MgSO4 and concentrated to obtain an oil, which was then subjected to silica gel column chromatography (90:10 hexane-ether), affording 25.0 g (yield 75%) of t-butyl 3-[4-(2-t-butoxycarbonylethyl)phenyl]propionate in the form of an oil.

Workup

  1. customThe organic layer was separated off
  2. extractionsubjected to extraction with ether
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto obtain an oil, which

Sources & evidence

ORD record
ord-6135dbb950ef4a7eb4135c7689cdb912
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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