Acetone → 6-(Hydroxymethyl)-2,3-dihydro-1H-inden-1-one

HRID 2377240Notes

Reaction equation

HRID 2377240 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C(=O)([O-])[O-:13].[K+].[K+].[CH3:18][C:19]([CH3:21])=[O:20]>O>[OH:13][CH2:11][C:1]1[CH:2]=[C:21]2[C:4]([CH2:3][CH2:18][C:19]2=[O:20])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 11430Potassium Carbonate

Product 1

HCID 211357856-(Hydroxymethyl)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Example 28 (8.0 g, 38.7 mmol) and p-toluenesulfonic acid (7.4 g, 38.7 mmol) in a mixture of water (20 mL) and acetone (85 mL) was heated to reflux for about 1 hour. The mixture was concentrated under vacuum, diluted with water, and neutralized by careful addition of potassium carbonate (2.7 g, 19.4 mmol). The precipitate was collected by filtration, washed with minimal water and diethyl ether, and dried under vacuum to provide the desired product. MS (DCI-NH3): m/z 180 (M+NH4)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 1 hour
  3. concentrationThe mixture was concentrated under vacuum
  4. additiondiluted with water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with minimal water and diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ddd5005a16b14830a0335f61a1857d1a
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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