Sulfuric Acid → 2-Butoxy-1-propanol

HRID 1638954Notes

Reaction equation

HRID 1638954 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 100 ml of ether and the mixture was stirred for 3 hours, and 12.7 g of (-)-ethyl-2-butoxypropionate was added dropwise thereto. After completion of the dropwise addition, stirring was continued for 15 minutes. Then, 50 ml of water and 50 ml of an aqueous 10% H2SO4 were added. The ether layer was separated and dried over MgSO4. After filtration, ether was evaporated. Yield: 7.4 g, optical rotation [α]D24° =+24.4°.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringstirring
  3. waitwas continued for 15 minutes
  4. customThe ether layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration, ether
  7. customwas evaporated
  8. customYield: 7.4 g, optical rotation [α]D24° =+24.4°

Sources & evidence

ORD record
ord-b91d6f08e123410f9feca4110b980b55
Source dataset
uspto-grants-1989_11
Patent number
US04882085

Reaction notes

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