Chlorosulfonic acid → 5-(2,6-Dimethyl-4-nitrophenoxy)-2-hydroxy-benzenesulfonic acid

HRID 1006715Notes

Reaction equation

HRID 1006715 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[CH:5]=[C:6]([CH3:16])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Cl[S:21]([OH:24])(=[O:23])=[O:22]>ClCCl>[CH3:16][C:6]1[CH:5]=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=[C:2]([CH3:1])[C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[C:13]([S:21]([OH:24])(=[O:23])=[O:22])[CH:14]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 140285904-(2,6-Dimethyl-4-nitrophenoxy)phenol

Product 1

HCID 226728575-(2,6-Dimethyl-4-nitrophenoxy)-2-hydroxy-benzenesulfonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title B compound, 3,5-dimethyl-4-(4′-hydroxyphenoxy)nitrobenzene (7.86 g, 30.35 mmol) in 150 mL of dichloromethane (CH2Cl2) is treated with chlorosulfonic acid (2.4 mL, 36.42 mmol) at RT. After 16 h, the reaction mixture is concentrated and the residue is dissolved in small amount of CH2Cl2 (ca. 5 mL). The product is precipitated by addition of brine (100 mL), collected by vacuum filtration, washed with water, hexanes and diethyl ether (Et2O) and dried in vacuo to give 5-(2,6-dimethyl-4-nitrophenoxy)-2-hydroxy-benzenesulfonic acid: NMR (DMSO-d6) 2.18 (s, 6H), 6.67-6.83 (m, 3H), 8.1 (s, 2H), 10.07 (s, 1H).

Workup

  1. concentrationthe reaction mixture is concentrated
  2. dissolutionthe residue is dissolved in small amount of CH2Cl2 (ca. 5 mL)
  3. customThe product is precipitated by addition of brine (100 mL)
  4. filtrationcollected by vacuum filtration
  5. washwashed with water, hexanes and diethyl ether (Et2O)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e22153e622df446584a991c4ab524c30
Source dataset
uspto-grants-2004_09
Patent number
US06790978B2

Reaction notes

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