Sodium Carbonate → HCID 23468921, compound

HRID 128300Notes

Reaction equation

HRID 128300 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[CH:18]1[C:19]2[C:2]3[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=3[O:8][C:9]=2[CH:10]=[CH:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 23468760HCID 23468760, compound

Product 1

HCID 23468921HCID 23468921, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

262.3 g (1 mol) of ethyl p-(2-oxocyclohexyloxy)-benzoate are cooled to 10° and 250 ml of concentrated sulfuric acid are added dropwise in the course of about 2 hours. During this addition, the temperature is kept at between 10° and 20° with an ice-water bath. When the addition has ended, the mixture is stirred at room temperature for a further 3 hours and then poured onto a 2:1 mixture of saturated aqueous sodium carbonate solution and ice. The aqueous phase is extracted once with about 1,000 ml of ether and then a further three times with 300 ml of ether each time and the combined organic phases are washed four times with 300 ml of 2 N sodium hydroxide solution each time, dried over sodium sulfate and evaporated under a waterpump vacuum. The oily residue is purified by filtration over a layer of silica gel, chloroform being used as the solvent and eluting agent. After evaporating off the chloroform, ethyl 6,7,8,9-tetrahydro-2-dibenzofurancarboxylate is obtained as a yellowish oil.

Workup

  1. additionDuring this addition
  2. customthe temperature is kept at between 10° and 20° with an ice-water bath
  3. additionWhen the addition
  4. extractionThe aqueous phase is extracted once with about 1,000 ml of ether
  5. washa further three times with 300 ml of ether each time and the combined organic phases are washed four times with 300 ml of 2 N sodium hydroxide solution each time
  6. dry with materialdried over sodium sulfate
  7. customevaporated under a waterpump vacuum
  8. filtrationThe oily residue is purified by filtration over a layer of silica gel, chloroform being
  9. washeluting agent
  10. customAfter evaporating off the chloroform

Sources & evidence

ORD record
ord-7424625bd206450f9ad8e989b2f79d3e
Source dataset
uspto-grants-1981_03
Patent number
US04259338

Reaction notes

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