Sulfuric Acid → 2-Butoxy-1-propanol

HRID 867362Notes

Reaction equation

HRID 867362 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][CH3:22])[CH3:17])C.OS(O)(=O)=O>O>[CH2:19]([O:18][CH:16]([CH3:17])[CH2:15][OH:14])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 13668406HCID 13668406, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 1776912-Butoxy-1-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.0 g of LiAlH4 was added to 62 ml of ether and the mixture was stirred for 3 hours. To the mixture was added dropwise 12.7 g of (-)-ethyl-2-butoxypropionate in the same manner as in Example 1, and the mixture was stirred for 15 minutes. Then, 50 ml of water and 50 ml of 10% H2SO4 aqueous solution were added thereto. The ther layer was separated, dried with MgSO4 and filtrated. Ether was distilled off toobtain the objective product at an yield of 7.4 g. The optical rotation [α]D24° was +24.4°.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customThe ther layer was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltrated
  5. distillationEther was distilled off toobtain the objective product at an yield of 7.4 g
  6. customwas +24.4°

Sources & evidence

ORD record
ord-795ffa9c8265417886af7d530b881137
Source dataset
uspto-grants-1988_10
Patent number
US04775223

Reaction notes

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