Sulfuric Acid → 3-Methyl-1-decanol

HRID 444334Notes

Reaction equation

HRID 444334 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([CH3:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>CCOCC>[CH3:14][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 560492Ethyl 3-methyldecanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 150549973-Methyl-1-decanolYield 88.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

740 g (3.46 mols) 3-methyl-decanoic acid ethyl ester, dissolved in 600 ml ether, are added while cooling to a suspension of 72 g (1.89 mols) lithium aluminium hydride in 600 ml ether. After the addition has ended the reaction mixture is heated for one hour to reflux temperature, is then hydrolysed and acidified with sulphuric acid. The organic phase is separated off, the aqueous phase is extracted with ether and the combined organic phases are freed from solvent. The destillation of the residue gives 529.5 g 3-methyldecanol (b.p.0.3 :83° C.), corresponding to a yield of 88.9% of theory.

Workup

  1. additionare added
  2. additionAfter the addition
  3. temperatureis heated for one hour
  4. temperatureto reflux temperature
  5. customThe organic phase is separated off
  6. extractionthe aqueous phase is extracted with ether

Sources & evidence

ORD record
ord-a609af37aa584653b6c9039ec5b44396
Source dataset
uspto-grants-1981_04
Patent number
US04263459

Reaction notes

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