M-Cresol → Cresatin

HRID 1901123Notes

Reaction equation

HRID 1901123 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].N1C=CC=CC=1.[C:15](Cl)([CH3:17])=[O:16]>C(Cl)Cl>[C:15]([O:7][C:6]1[CH:1]=[C:2]([CH3:8])[CH:3]=[CH:4][CH:5]=1)(=[O:16])[CH3:17]

Participants

5

Reactant 3

HCID 342M-CresolHCID 1049PyridineHCID 6367Acetyl chloride

Product 1

HCID 67406Cresatin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of m-cresol (Aldrich) (80 g, 0.74 mol) in dry CH2Cl2 (300 mL) and pyridine (71 mL, 0.89 mol) at 0° C. was added dropwise AcCl (58 mL, 0.81 mol). The reaction mixture was stirred for ca 1 h and then diluted with more CH2Cl2. The organic phase was washed successively with HCl 1N (3×), brine, dried over MgSO4 and evaporated. The residue was distilled under vacuum to give the title compound.

Workup

  1. washThe organic phase was washed successively with HCl 1N (3×), brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-bdab9ef016894d6788b0e73c543a41a7
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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