2,4-Dichlorophenol → 2,6-Bis(3,5-dichloro-2-hydroxybenzyl)-4-fluorophenol

HRID 894224Notes

Reaction equation

HRID 894224 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[C:5]([OH:10])=[C:4]([CH2:11]O)[CH:3]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[OH:21]>C(O)(=O)C.OS(O)(=O)=O>[Cl:13][C:14]1[C:15]([OH:21])=[C:16]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:11][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([CH2:8][C:16]2[CH:17]=[C:18]([Cl:20])[CH:19]=[C:14]([Cl:13])[C:15]=2[OH:21])[C:5]=1[OH:10]

Participants

5

Reactant 2

HCID 84492,4-DichlorophenolHCID 23935454-Fluoro-2,6-bis(hydroxymethyl)phenol

Product 1

HCID 130642162,6-Bis(3,5-dichloro-2-hydroxybenzyl)-4-fluorophenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

4-fluoro-2,6-bis(hydroxymethyl)phenol (2.0 g) was dissolved in glacial acetic acid (20 ml) and added slowly to 2,4-dichlorophenol (3.8 g) in concentrated H2SO4 at 60°-70°. The mixture was held at 65°-70° for 1 hr, cooled, acetic acid (20 ml) was added to dissolve the solids and the solution was poured into ice-water. The solid precipitate was purified by column chromatography over silica gel using hexane-ethyl acetate as eluent. The title compound was obtained in yield of 1.3 g, mp 168°.

Workup

  1. temperaturecooled
  2. dissolutionto dissolve the solids
  3. customThe solid precipitate was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-5f5fe0e7596c4c8884552faf5fc3a3fc
Source dataset
uspto-grants-1981_08
Patent number
US04282390

Reaction notes

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