Water → HCID 54363126, compound

HRID 264411Notes

Reaction equation

HRID 264411 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH3:12][CH:13](O)[CH:14]=[CH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:12]([CH:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=2)[C:8]1=[O:11])[CH:13]=[CH:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 54363126HCID 54363126, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 16 g of 6-hydroxy-1-indanone, 22.3 ml of 3-buten-2-ol and 160 mg of p-toluenesulfonic acid in 170 ml of 2,2-dimethoxy-propane was boiled under reflux for 38 hours on a water separator filled with molecular sieve (0.4 nm, 2 mm pearl shaped). The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/ethyl acetate 4:1). In addition to 7.5 g of educt, there were obtained 6.21 g (28%) of (RS)-2-(2-buten-1-yl)-6-hydroxy-1-indanone as a yellow oil.

Workup

  1. additionseparator filled with molecular sieve (0.4 nm, 2 mm pearl shaped)
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 4:1)
  4. additionIn addition to 7.5 g of educt

Sources & evidence

ORD record
ord-f19084412d47464cb1f7e6d985171ca9
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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