Water → 3-chloro-5-fluoro-2-hydroxybenzaldehyde

HRID 1163962Notes

Reaction equation

HRID 1163962 reaction equation
[OH-:1].[Na+].[OH2:3].[Cl:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1O.[CH:13](Cl)(Cl)Cl>>[Cl:4][C:5]1[C:6]([OH:3])=[C:7]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH:13]=[O:1]

Participants

5

Reactant 4

HCID 962WaterHCID 6212Chloroform2×HCID 14798Sodium HydroxideHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 27827493-chloro-5-fluoro-2-hydroxybenzaldehyde

Procedure

Sodium hydroxide (50 g.) was dissolved in 70 ml. of water. 2-Chloro-4-fluorophenol (10 g., 0.068 mole) was added and then chloroform (30 ml.) The mixture was refluxed for two hours. Addition of chloroform (30 ml.) and reflux for 2 hours was twice repeated. The reaction mixture was cooled to room temperature and crude product recovered as the sodium salt by filtration. The crude was taken into water and acidified with 1 N hydrochloric acid to yield product (6.6 g.) in the free phenolic form. The latter was chromatographed on 200 g. of silica gel, with 1:1 methylene chloride: hexane as eluant. The column was monitored by tlc. Clean product containing fractions were combined and evaporated to dryness to yield purified 3-chloro-5-fluoro-2-hydroxybenzaldehyde [3.08 g.; m.p. 81°-83° C., Rf 0.49 (1:1 methylene chloride: hexane); ir (CH2Cl2)1658, 1460, 1439, 1289, 1230, 1116 cm-1 ].

Workup

  1. temperaturereflux for 2 hours
  2. filtrationcrude product recovered as the sodium salt by filtration
  3. customto yield product (6.6 g.) in the free phenolic form
  4. customThe latter was chromatographed on 200 g
  5. additioncontaining fractions
  6. customevaporated to dryness
  7. customto yield
  8. custompurified 3-chloro-5-fluoro-2-hydroxybenzaldehyde [3.08 g.; m.p. 81°-83° C., Rf 0.49 (1:1 methylene chloride: hexane); ir (CH2Cl2)1658, 1460, 1439, 1289, 1230, 1116 cm-1 ]

Sources & evidence

ORD record
ord-644f8add5c7d4fbf894b1b8aaca4c49b
Source dataset
uspto-grants-1983_01
Patent number
US04367234

Reaction notes

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