3-Chloro-2-methyl-1-propene → HCID 10752120, compound

HRID 964807Notes

Reaction equation

HRID 964807 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([OH:17])=[C:12]([CH3:18])[C:11]=1[CH3:19])=[O:8].[CH2:20](Cl)[C:21](=[CH2:23])[CH3:22]>CN(C)C=O>[CH:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:22][C:21]([CH3:23])=[CH2:20])=[C:12]([CH3:18])[C:11]=1[CH3:19])=[O:8]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 21961295N-(4-hydroxy-2,3,6-trimethylphenyl)formamide

Product 1

HCID 10752120HCID 10752120, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (74.0 g, 0.54 mol) was added to a solution of 4-formylamino-2,3,5-trimethylphenol (85.5 g, 0.48 mol) and methallyl chloride (45.3 g, 0.5 mol) in dimethylformamide (300 ml) and the mixture was stirred at 80° C. for 3 hours under an argon atmosphere. The reaction mixture was poured into ice-cold water. Crystals precipitated were filtered, washed with water and dried. The crude crystals obtained were recrystallized from isopropyl ether to obtain the desired compound (80.0 g, yield: 71.6%), m.p. 144°-145° C.

Workup

  1. additionThe reaction mixture was poured into ice-cold water
  2. customCrystals precipitated
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried
  6. customThe crude crystals obtained
  7. customwere recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-357cd725e8694bcfb121dcae138ffccc
Source dataset
uspto-grants-1998_06
Patent number
US05770772

Reaction notes

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