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Sulfuric Acid → 4-(chloromethyl)-7-hydroxy-8-methyl-2H-chromen-2-one

HRID 591536
Notes
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Reaction equation

HRID 591536 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].OS(O)(=O)=O.[CH3:16][C:17]1[C:22]([OH:23])=[CH:21][CH:20]=CC=1O>O>[Cl:1][CH2:2][C:3]1[C:9]2[C:8](=[C:17]([CH3:16])[C:22]([OH:23])=[CH:21][CH:20]=2)[O:7][C:5](=[O:6])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 118432-MethylresorcinolHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 54238774-(chloromethyl)-7-hydroxy-8-methyl-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To ethyl 4-chloro-3-oxobutanoate (5.77 mL) was added conc.H2SO4 (15.03 mL) at 0° C. Then to the mixture was added 2-methylbenzene-1,3-diol (5.0 g) in several portions at 0° C. The mixture was stirred at 0° C. for 30 min. The mixture was warmed to room temperature for 1.5 h. The reaction mixture was poured into water under stirring at 0° C. The precipitate was collected by filtration and washed with water to give the title compound (8.58 g).

Workup

  1. customat 0° C
  2. temperatureThe mixture was warmed to room temperature for 1.5 h
  3. stirringunder stirring at 0° C
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-dd1809bdb7b542039af18c65a0fabc65
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238639B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes