Ethanol → HCID 20330120, compound

HRID 2057725Notes

Reaction equation

HRID 2057725 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]C=O.[CH:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])OCC.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O.C(OCC)C>[CH2:20]([O:19][CH:12]([O:16][CH2:17][CH3:18])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH3:21]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 31214Ethyl orthoformateHCID 22600516HCID 22600516, compound

Product 1

HCID 20330120HCID 20330120, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

12.0 gms of 9-chloro-nonaldehyde was heated at reflux with 20 gms of triethyl orthoformate, 9 gms anhydrous ethanol and one drop of concentrated sulphuric acid for one hour. The reaction was cooled, 10 gms of sodium carbonate was added and the mixture stirred 10 minutes. The mixture was diluted with 100 mls of diethyl ether and extracted twice with 50 mls of saline solution. The organic layer was dried over sodium sulphate, concentrated on rotary evaporator and distilled. The major fraction distilled at 84° at 0.1 torr yielding 13.3 gms of 1,1-diethoxy-9-chloro nonane. N.M.R. (CdCl3): triplet 4.47 ppm (1H), multiplet 3.58 ppm (6H), triplet 1.21 ppm.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted twice with 50 mls of saline solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated on rotary evaporator
  5. distillationdistilled
  6. distillationThe major fraction distilled at 84° at 0.1 torr

Sources & evidence

ORD record
ord-70bdc8a1050147b88698ccb704fb4f8e
Source dataset
uspto-grants-1980_07
Patent number
US04212830

Reaction notes

Loading…