Water → HCID 54333761, compound

HRID 264444Notes

Reaction equation

HRID 264444 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][C:5]2([CH3:15])[CH3:14].[CH3:16][CH:17](O)[CH:18]=[CH2:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:16]([CH:6]1[C:5]([CH3:15])([CH3:14])[C:4]2[C:8](=[CH:9][C:10]([O:11][CH3:12])=[C:2]([Cl:1])[CH:3]=2)[C:7]1=[O:13])[CH:17]=[CH:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 19036563HCID 19036563, compound

Product 1

HCID 54333761HCID 54333761, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 14.5 g of 5-chloro-6-methoxy-3,3-dimethyl-1-indanone, 13.3 ml of 3-buten-2-ol and 300 mg of p-toluenesulfonic acid in 150 ml of 2,2-dimethoxy-propane was boiled under reflux for 71 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/diethyl ether 6:1). In addition to 2.25 g of educt, there were obtained 11.9 g (66%) of (RS)-2-(2-buten-1-yl)-5-chloro-6-methoxy-3,3-dimethyl-1-indanone as a pale yellow solid with m.p. 86°.

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/diethyl ether 6:1)
  4. additionIn addition to 2.25 g of educt

Sources & evidence

ORD record
ord-45b02b7b06f64419ab7cb97abf1434f6
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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