Dodecanoyl chloride → HCID 86592258, compound

HRID 1611895Notes

Reaction equation

HRID 1611895 reaction equation
[Cl:1][C:2]1[C:3](=[O:14])[O:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[C:7]([OH:13])[CH:6]=2.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.[C:28](Cl)(=O)[CH2:29][CH2:30]CCCCCCCCC>O1CCCC1.C(OCC)(=O)C.O>[C:3]([OH:4])(=[O:14])[CH2:2][CH2:11][CH2:10][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:28][CH2:29][CH3:30].[Cl:1][C:2]1[C:3](=[O:14])[O:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[C:7]([OH:13])[CH:6]=2

Participants

8

Reactant 4

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 53550793-Chloro-7-hydroxy-4-methyl-2-benzopyrone

Product 1

HCID 86592258HCID 86592258, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 g of 3-chloro-4-methyl-7-hydroxy coumarin was dissolved in 60 ml of tetrahydrofuran in a 250 ml flask, followed by the addition of 3.6 g of potassium carbonate and 3.6 ml of triethylamine. After 30 minutes, 8.0 ml of lauroyl chloride was added thereto and the mixture was stirred for 2 hours at room temperature. Thereafter, 50 ml of distilled water and 250 ml of ethyl acetate were added to extract the title compound into the ethyl acetate phase. The ethyl acetate phase was washed with 200 ml of salt water, and then dried with anhydrous manganese. Following the distillation and evaporation of the solvent, the residue was recrystalized with hexane and ethyl acetate to obtain white 3-chloro-4-methyl-7-hydroxy coumarin laurate.

Workup

  1. extractionto extract the title compound into the ethyl acetate phase
  2. washThe ethyl acetate phase was washed with 200 ml of salt water
  3. dry with materialdried with anhydrous manganese
  4. distillationthe distillation and evaporation of the solvent
  5. customthe residue was recrystalized with hexane and ethyl acetate

Sources & evidence

ORD record
ord-a109dfee3478408387f7f6789f328bc1
Source dataset
uspto-grants-2006_01
Patent number
US06991914B2

Reaction notes

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