Acetone → 7-Hydroxymethylcoumarin

HRID 1090760Notes

Reaction equation

HRID 1090760 reaction equation
CC(C)=[O:3].Br[CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>O>[OH:3][CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 2641197-(Bromomethyl)-2h-chromen-2-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 150282577-Hydroxymethylcoumarin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1:1 mixture of acetone and water (560 ml) was added 7-bromomethy1coumarin (7.0 g, 29.3 mmol). The resulting suspension was refluxed for 48 hrs at which time the reaction mixture became a clear solution. The solution was then cooled and neutralized with sodium bicarbonate (2.4 g, 29.3 mmol) and concentrated in vacuo to about 65 ml. A thick mass of crystals resulted. The crystals were collected by filtration to yield 5.27 g of product after drying in vacuo (100% of theory). The melting point was 116°-117° C.

Workup

  1. temperatureThe resulting suspension was refluxed for 48 hrs at which time the reaction mixture
  2. temperatureThe solution was then cooled
  3. concentrationconcentrated in vacuo to about 65 ml
  4. customA thick mass of crystals resulted
  5. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-10bd2cab9400439a9ff0ac45b562a8d9
Source dataset
uspto-grants-1992_01
Patent number
US05082934

Reaction notes

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