1-Butanol → HCID 18728491, compound

HRID 842962Notes

Reaction equation

HRID 842962 reaction equation
[C@@H:1]1([C:8]([OH:10])=[O:9])[CH2:4][CH2:3][C@@H:2]1[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH2:16](O)[CH2:17][CH2:18][CH3:19]>>[C@@H:1]1([C:8]([O:10][CH2:4][CH2:1][CH2:2][CH3:3])=[O:9])[CH2:4][CH2:3][C@@H:2]1[C:5]([O:7][CH2:16][CH2:17][CH2:18][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 6544483(1R,2S)-cyclobutane-1,2-dicarboxylic acid

Product 1

HCID 18728491HCID 18728491, compound

Procedure

1 g (6.94 mmol) of cis-cyclobutane-1,2-dicarboxylic acid in 50 ml of n-butanol were heated under reflux with 0.3 g of conc. H2SO4 for 90 min. The mixture was then concentrated to about 5 ml and poured into dil. NaHCO3 solution, extracted with ethyl acetate, dried over sodium sulphate and concentrated. Purification was carried out chromatographically over silica gel (mobile phase: petroleum ether:ethyl acetate 100:2>100:5).

Workup

  1. concentrationThe mixture was then concentrated to about 5 ml
  2. additionpoured into dil. NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-6521c4d4f9b140dbb1d3ff7b219803de
Source dataset
uspto-grants-2002_04
Patent number
US06376539B1

Reaction notes

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