3-Hydroxybenzaldehyde → 2-Chloro-3-hydroxybenzaldehyde

HRID 1766035Notes

Reaction equation

HRID 1766035 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(O[Cl:15])(C)(C)C>CC(O)=O>[Cl:15][C:3]1[C:2]([OH:1])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 5933762-Chloro-3-hydroxybenzaldehydeYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 3-hydroxybenzaldehyde (20.12 g, 160 mmol) in HOAc (40 mL) was added carefully tBuOCl (20 mL, 176 mmol) with stirring. The reaction became a clear solution and strongly exothermic. It was allowed to cool and stirred for 16 hours, resulting in a white precipitate. The solid was filtered, washed with H2O and dried to give 2-chloro-3-hydroxybenzaldehyde (13.77 g, 55%), GCMS (EI) m/z 156, 158 (M+).

Workup

  1. temperatureto cool
  2. stirringstirred for 16 hours
  3. customresulting in a white precipitate
  4. filtrationThe solid was filtered
  5. washwashed with H2O
  6. customdried

Sources & evidence

ORD record
ord-287439529d1649998e1e4819d7798ea8
Source dataset
uspto-grants-2007_06
Patent number
US07229995B2

Reaction notes

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