Sulfuric Acid → 2,9-Diethyl-2,9-dimethyldecane-1,10-diol

HRID 1262827Notes

Reaction equation

HRID 1262827 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]([CH3:26])([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH2:24][CH3:25])([CH3:23])[C:20](O)=[O:21])[C:10](O)=[O:11])[CH3:8].S(=O)(=O)(O)O>C(OCC)C>[CH2:24]([C:19]([CH3:23])([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:9]([CH2:7][CH3:8])([CH3:26])[CH2:10][OH:11])[CH2:20][OH:21])[CH3:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 30696932,9-Diethyl-2,9-dimethyldecanedioic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 30696792,9-Diethyl-2,9-dimethyldecane-1,10-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1.6 grams (0.0425 mole) of lithium aluminum hydride in 40 ml of anhydrous diethyl ether was added, under vigorous stirring, with a solution of 4.87 grams (0.0170 mole) of 2,9-diethyl-2,9-dimethyl-1,10-decanedioic acid, and the resulting mixture was refluxed for 1 hour. After cooling to room temperature, the suspension was added with 12 ml of a 25% (v/v) aqueous solution of sulphuric acid. The obtained precipitate was removed by filtration and the filtrate was poured into 50 ml of a 20% aqueous solution of sodium carbonate under cooling and stirring. The organic layer was separated, washed with water, dried over anhydrous sodium sulphate and evaporated to dryness under vacuum. 4.0 Grams (90.5% of theoretical) of the chromatographycally pure title compound were obtained.

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. customThe obtained precipitate was removed by filtration
  3. additionthe filtrate was poured into 50 ml of a 20% aqueous solution of sodium carbonate
  4. temperatureunder cooling
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-6f8b39f8b994402591c366e1f6f620c9
Source dataset
uspto-grants-1984_06
Patent number
US04454145

Reaction notes

Loading…