Dichloromethane → 5-Methyl-3-(3-pyridinylsulfonyloxy)phenol

HRID 442970

Reaction equation

HRID 442970 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:13]=1.ClCCl>C(=O)(O)[O-].[Na+]>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:18]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)(=[O:20])=[O:19])[CH:3]=[C:4]([OH:5])[CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 12571517Pyridine-3-sulfonyl chloride hydrochloride

Product 1

HCID 544756955-Methyl-3-(3-pyridinylsulfonyloxy)phenolYield 58.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of orcinol monohydrate (1.42 g, 0.01 mol) and 3-pyridylsulfonyl chloride hydrochloride (2.13 g, 0.01 mol), as prepared in J. Am. Chem. Soc., 114:4889 (1992), in saturated aqueous sodium bicarbonate (17.5 mL) and dichloromethane (50 mL) was stirred rapidly at ambient temperature for 2 days. The dichloromethane was separated and the aqueous layer was extracted with ethyl acetate (3×25 mL). The ethyl acetate and dichloromethane extracts were combined and washed with brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was recrystallized from ether and hexane, collected by filtration, and dried under high vacuum to give 1.54 g of a white solid (58% yield). 1H-NMR (300 MHz, CDCl3) δ 9.03 (d, 1H), 8.88 (dd, 1H), 8.16 (dt, 1H), 7.5 (m, 1H), 6.57 (d, 1H), 6.42 (s, 1H), 6.32 (t, 1H), 2.24 (s, 3H).

Workup

  1. customas prepared in J
  2. customThe dichloromethane was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×25 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was recrystallized from ether and hexane
  8. filtrationcollected by filtration
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-a7647b352ca74818b082d564aa5e5e97
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Linked notes

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