Acetone → HCID 67206335, compound

HRID 1023855Notes

Reaction equation

HRID 1023855 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([C:10]=1[OH:11])[C:7]([OH:9])=[O:8].[CH3:13][C:14]([CH3:16])=O.S(Cl)(Cl)=O>COCCOC.CN(C1C=CN=CC=1)C.O.C([O-])([O-])=O.[K+].[K+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:12][C:14]([CH3:16])([CH3:13])[O:8][C:7](=[O:9])[C:6]=2[C:10]=1[OH:11]

Participants

8

Reactant 3

HCID 180AcetoneHCID 24386Thionyl ChlorideHCID 36531173-chloro-2,6-dihydroxybenzoic acid

Product 1

HCID 67206335HCID 67206335, compoundYield 27%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 5-chloro-2,6-dihydroxybenzoic acid (Doyle, F. P. J. Chem. Soc., 1963, p. 497-506) (500 mg, 2.65 mmol) in DME (2 mL) was added DMAP (16.2 mg, 0.13 mmol) and acetone (200.2 mg, 3.45 mmol). The solution was cooled to 10° C. and thionyl chloride (448 mg, 3.77 mmol) was added over 10 min. The solution was allowed to overnight. The solution was diluted with water and neutralized with solid K2CO3 and the aqueous phase was extracted w/EtOAc. The combined organic layers were washed with water, brine and dried (Na2SO4). The crude residue was purified by column chromatography on silica gel to afford the product as yellow solid (162 mg, 27% yield). 1H NMR: 1.74 (s, 6H), 6.44 (d, 1H, J=8.0 Hz), 7.48 (d, 1H, J=8.0 Hz), 10.83 (s, 1H).

Workup

  1. extractionthe aqueous phase was extracted w/EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customThe crude residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-70b74ac15ab64e2a8dd917adf25b2b53
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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