Sodium Chloride → HCID 86737019, compound

HRID 1706047Notes

Reaction equation

HRID 1706047 reaction equation
Br[CH:2](Br)[C@@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([O:10][CH3:11])=[O:9].[O:13]1CCCC1.[Cl-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>[N+]([O-])([O-])=O.[Ag+].O>[CH:2]([C@@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([O:10][CH3:11])=[O:9])=[O:13]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 86737020HCID 86737020, compound

Product 1

HCID 86737019HCID 86737019, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

A solution of 25 g. (83.3 mmoles) of trans-2-dibromomethyl-1-cyclopentanecarboxylic acid, methyl ester [prepared as described in Chem. Ber. 110, 1823 (1977), from cyclopentene and dibromoketene] in 140 ml. of tetrahydrofuran is heated to reflux in a nitrogen atmosphere. While stirring, a solution of 33.0 g. (194 mmole) of silver nitrate in 55 ml. of water is added over a period of ten minutes. After an additional thirty minutes of heating and stirring the mixture is cooled and saturated aqueous sodium chloride solution is added. The mixture is then neutralized with saturated aqueous sodium carbonate solution and the insoluble salts are removed by filtration through a Celite (diatomaceous earth) pad. The pad is washed with ether and some solid sodium chloride is added to the filtrate. The layers are separated and the aqueous portion is reextracted twice with ether. The combined organic layers are dried over magnesium sulfate, filtered and taken to dryness in vacuo leaving 7.5 g. of amber oil. This is distilled at reduced pressure collecting 4.1 g. (32%) of product, trans-2-formylcyclopentanecarboxylic acid, methyl ester, boiling at 60°-85°/0.4 mm.

Workup

  1. temperatureto reflux in a nitrogen atmosphere
  2. temperatureAfter an additional thirty minutes of heating
  3. stirringstirring the mixture
  4. temperatureis cooled
  5. customthe insoluble salts are removed by filtration through a Celite (diatomaceous earth) pad
  6. washThe pad is washed with ether
  7. additionsome solid sodium chloride is added to the filtrate
  8. customThe layers are separated
  9. dry with materialThe combined organic layers are dried over magnesium sulfate
  10. filtrationfiltered
  11. customleaving 7.5 g
  12. distillationThis is distilled at reduced pressure
  13. customcollecting 4.1 g

Sources & evidence

ORD record
ord-77b4982b3fd54bb09dd9c34f997fc137
Source dataset
uspto-grants-1980_06
Patent number
US04206137

Reaction notes

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