Sodium Carbonate → HCID 21312660, compound

HRID 971932Notes

Reaction equation

HRID 971932 reaction equation
[OH:1][CH:2]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])/[CH:3]=[CH:4]/[CH:5]1[CH2:7][C:6]1([C:12]([O:14][CH3:15])=[O:13])[C:8]([O:10][CH3:11])=[O:9].O.[C:22]1(C)C=[CH:26][C:25](S(O)(=O)=O)=[CH:24][CH:23]=1.C([O-])([O-])=[O:34].[Na+].[Na+]>O1C=CCCC1>[O:34]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:1][CH:2]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])/[CH:3]=[CH:4]/[CH:5]1[CH2:7][C:6]1([C:8]([O:10][CH3:11])=[O:9])[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 21312640HCID 21312640, compound

Product 1

HCID 21312660HCID 21312660, compound

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

A solution of dimethyl trans-2-(3-hydroxy-1-octenyl)cyclopropane-1,1-dicarboxylate (22.4 g), described in Example 42, dihydropyran (80 ml, distilled over sodium) and p-toluenesulfonic acid monohydrate (300 mg) is allowed to stand at room temperature for 30 min. After adding a few ml of 10% Na2CO3 solution the mixture is extracted with ether. The ether extract is washed with water, dried (Na2SO4) and evaporated. Purification of the residue by chromatography on silica gel gives the title compound.

Workup

  1. extractionis extracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customPurification of the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-392f876089ef4ec584dfbc62a065d951
Source dataset
uspto-grants-1979_07
Patent number
US04161608

Reaction notes

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