Sulfuric Acid → HCID 13685447, compound

HRID 867366Notes

Reaction equation

HRID 867366 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.C([O:14][C:15](=O)[CH:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH3:17])C.OS(O)(=O)=O>O>[CH2:19]([O:18][CH:16]([CH3:17])[CH2:15][OH:14])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 14793561HCID 14793561, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13685447HCID 13685447, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.5 g of LiAlH4 was added to 150 ml of ether and the mixture was stirred for 3.5 hours. To the mixture was added dropwise 38.8 g of (-)-ethyl-2-octadecyloxypropionate in the same manner as in Example 6, andthe mixture was stirred for 20 minutes. Then, 50 ml of water was added thereto and 10% H2SO4 aqueous solution was further added to give a pH of 7-8. The ether layer was separated, dried with MgSO4 andfiltrated. Ether was distilled off and the residue was subjected to distillation under reduced pressure, whereby 14.0 g of (+)-2-octadecyloxypropanol was obtained by collecting a fraction of 175°-179° C./0.9 mmHg.

Workup

  1. stirringandthe mixture was stirred for 20 minutes
  2. customto give a pH of 7-8
  3. customThe ether layer was separated
  4. dry with materialdried with MgSO4
  5. distillationEther was distilled off
  6. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-460e39be235d4535a4c5f3cde0674c96
Source dataset
uspto-grants-1988_10
Patent number
US04775223

Reaction notes

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