Hydrochloric Acid → Cresatin

HRID 1383866Notes

Reaction equation

HRID 1383866 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=CC=1.Cl>O>[C:9]([O:7][C:6]1[CH:1]=[C:2]([CH3:8])[CH:3]=[CH:4][CH:5]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 342M-CresolHCID 1049PyridineHCID 7918Acetic Anhydride

Product 1

HCID 67406CresatinYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Meta-cresol (1 g, 9.0 mmol) and acetic anhydride (1.1 g, 10.8 mmol) were mixed in the presence of pyridine (3 ml) as a base at 0° C., and gradually heated to room temperature. After 30 minutes, 10˜15 ml of water is added thereto, and the mixture was neutralized by adding 1N HCl (30 ml) in three portions. The resultant mixture was extracted with organic solvent, washed, dried and purified by using column chromatography (eluent: hexane/ethyl acetate=6/1) to obtain 1.3 g (96%) of compound (3).

Workup

  1. extractionThe resultant mixture was extracted with organic solvent
  2. washwashed
  3. customdried
  4. custompurified

Sources & evidence

ORD record
ord-2df4a5d6ecae44c784e6216f4ff7a112
Source dataset
uspto-grants-2001_07
Patent number
US06255517B1

Reaction notes

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