Water → 7-Chloro-1,3-dioxaindane-5-carbaldehyde

HRID 705700Notes

Reaction equation

HRID 705700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].[C:12]([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[C:9]2[O:10][CH2:12][O:11][C:8]=2[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 24681823-Chloro-4,5-dihydroxybenzaldehyde

Product 1

HCID 6764927-Chloro-1,3-dioxaindane-5-carbaldehydeYield 412.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-chloro-4,5-dihydroxy-benzaldehyde (8.0 g, 46 mmol) and BrClCH2 (89 g, 0.70 mol) in dry DMF (300 mL) was added Cs2CO3 (228 g, 0.700 mol). The mixture was stirred at 60° C. overnight and was then poured into water. The resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the title compound (35.0 g; 100%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1dbf80a588e649d3afa474af64697a63
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

Loading…