Methyl 3,5-Dihydroxybenzoate → HCID 53882575, compound

HRID 482097Notes

Reaction equation

HRID 482097 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[OH:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([OH:23])[CH:22]=1)[C:16]([O:18][CH3:19])=[O:17]>C(=O)(O)[O-].[Na+].C(OCC)C.C(Cl)Cl>[OH:12][C:13]1[CH:22]=[C:21]([O:23][S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:9])[CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=1

Participants

6

Reactant 2

HCID 75076Methyl 3,5-DihydroxybenzoateHCID 761872-Chlorobenzenesulfonyl chloride2×

Product 1

HCID 53882575HCID 53882575, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Chlorobenzenesulfonyl chloride (2.49 g, 0.018 mol) was added dropwise to a rapidly stirred mixture of methyl 3,5-dihydroxybenzoate in saturated sodium bicarbonate (20 mL) and diethyl ether (20 mL) and allowed to stir at ambient temperature. After 2 days, 1.25 g of 2-chlorobenzenesulfonyl chloride was added and stirred for an additional 1 day. The reaction mixture was diluted with methylene chloride and separated. The aqueous layer was extracted with methylene chloride. The combined methylene chloride extracts were washed with brine and water, dried, and evaporated to an oil. The oil was triturated with hexanes (4 times) before placing the residual oil on a silica gel column and eluted first with methylene chloride, then 10% ethyl acetate/methylene chloride. The appropriate fractions were evaporated to give 1.35 g of solid.

Workup

  1. stirringstirred for an additional 1 day
  2. customseparated
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. washThe combined methylene chloride extracts were washed with brine and water
  5. customdried
  6. customevaporated to an oil
  7. customThe oil was triturated with hexanes (4 times)
  8. washeluted first with methylene chloride
  9. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-f071d3368ebd4c398cbe2d73690aeff2
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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