Formaldehyde → 2,4-dichloro-6-(hydroxymethyl)phenol

HRID 1462964Notes

Reaction equation

HRID 1462964 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-:10].[Na+].[CH2:12]=O>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([OH:9])=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[CH2:12][OH:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 84492,4-DichlorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 2411962,4-dichloro-6-(hydroxymethyl)phenol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 2,4-dichlorophenol (15.3 g), 10% sodium hydroxide solution (100 ml) and 40% aqueous formaldehyde solution (37.5 ml) was heated at 95°-100° C. for 4 hr, then cooled and acidified by addition of 2-normal sulphuric acid (70 ml). The precipitated oil was extracted into toluene, and the extract washed with sodium bicarbonate solution, dried and evaporated. The residue was recrystallised from boiling water to yield 3,5-dichloro-2-hydroxybenzyl alcohol (4.0 g), m.p. 81°-82° C. on drying at 56° C./20 mm. Hg=2660 Pa.

Workup

  1. temperaturewas heated at 95°-100° C. for 4 hr
  2. temperaturecooled
  3. extractionThe precipitated oil was extracted into toluene
  4. washthe extract washed with sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customThe residue was recrystallised

Sources & evidence

ORD record
ord-3ada45b6e1414c3daf08adc4c2c5dc3f
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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