Sodium Iodide → HCID 20131465, compound

HRID 845491Notes

Reaction equation

HRID 845491 reaction equation
[C:1]([CH:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:14])([O:3][CH2:4][CH3:5])=[O:2].[I-].[Na+].[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1.O>[C:1]([C:6]1([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:14])([O:3][CH2:4][CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 227421Ethyl 2-oxo-1-cyclooctanecarboxylate

Product 1

HCID 20131465HCID 20131465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-carboethoxy-cyclooctanone (92.2 g, 0.5 mole) in toluene (1.6 l) is treated with sodium iodide (1 g) and 60% sodium hydride in mineral oil (23.3 g, 0.58 mole). The mixture is heated at 110° C. The mixture is treated with ethyl α-bromoacetate (98.0 g, 0.58 mole) dropwise and the mixture is warmed to 65° C. for 18 hours. The mixture is cooled and water (500 ml) was added. The layers are separated and the aqueous is extracted with toluene (2×1 l). The extracts are dried (MgSO4) and filtered. The filtrate is concentrated at reduced pressure and distilled to yield pure 2-carboethoxy-2-carboethoxymethylcyclooctanone with a bp of 193°-195° C. at 16 mm.

Workup

  1. temperaturethe mixture is warmed to 65° C. for 18 hours
  2. temperatureThe mixture is cooled
  3. customThe layers are separated
  4. extractionthe aqueous is extracted with toluene (2×1 l)
  5. dry with materialThe extracts are dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated at reduced pressure
  8. distillationdistilled

Sources & evidence

ORD record
ord-44c55df09a9341df816c6772ad78cc22
Source dataset
uspto-grants-1988_07
Patent number
US04758585

Reaction notes

Loading…