2-Methylresorcinol → 4-chloro-2-methyl-benzene-1,3-diol

HRID 1983427Notes

Reaction equation

HRID 1983427 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].[Cl:10]N1C(=O)CCC1=O>CO>[Cl:10][C:7]1[CH:6]=[CH:5][C:3]([OH:4])=[C:2]([CH3:1])[C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 118432-MethylresorcinolHCID 31398Chlorosuccinimide

Product 1

HCID 112059244-chloro-2-methyl-benzene-1,3-diolYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methylresorcinol (40 g, 322 mmol) in 750 ml of methanol was added (45.17 g, 0.338 mol) of N-chlorosuccinimide. The mixture was stirred for 6 hours. The solvent was evaporated and the resulting solid was triturated in 500 ml of a 2:1 mixture of hexane and ethyl acetate. The brown crystalline precipitate (succinimide) was filtered off and rinsed with a little extra solvent. The filtrate was concentrated to give the crude product, which was further purified on silica eluting with 4:1 hexanes/ethyl acetate. Appropriate fractions were combined, and evaporated. The product was crystallized from about 1:8 ether/hexanes to afford 33.1 g (65%) of the desired substituted resorcinol 15b. 1H NMR (DMSO-d6) δ: 9.38 (s, 1H), 8.83 (s, 1H), 6.92 (d, J=8.5 Hz, 1H), 6.33 (d, J=8.5 Hz, 1H), 2.00 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting solid was triturated in 500 ml of a 2:1 mixture of hexane and ethyl acetate
  3. filtrationThe brown crystalline precipitate (succinimide) was filtered off
  4. washrinsed with a little extra solvent
  5. concentrationThe filtrate was concentrated
  6. customto give the crude product, which
  7. customwas further purified on silica eluting with 4:1 hexanes/ethyl acetate
  8. customevaporated
  9. customThe product was crystallized from about 1:8 ether/hexanes

Sources & evidence

ORD record
ord-84e1fabfdb0c434da55254bfc26d74a7
Source dataset
uspto-grants-2009_06
Patent number
US07541454B2

Reaction notes

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