Acetone → HCID 59726037, compound

HRID 336429Notes

Reaction equation

HRID 336429 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[O:15][CH3:16].[CH3:17]C(C)=O.C([O-])([O-])=O.[K+].[K+].IC>O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59726101HCID 59726101, compound

Product 1

HCID 59726037HCID 59726037, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To the phenol 1-7 (10.4 g, 39.1 mmol) in HPLC grade acetone (150 mL) was added K2CO3 (15 g, 108.5 mmol) and iodomethane (5 mL, 80.3 mmol). The reaction was heated to 60° C. for 22 h. The flask was cooled and then H2O (40 mL) was added and the mixture stirred for 30 min. The volatiles were removed in vacuo and the residue was taken up in CH2Cl2 and H2O. After extracting into CH2Cl2 (×3), the combined organic layers were washed with H2O, dried over Na2SO4, filtered and concentrated to give the methyl ester 2-2 as an orange oil (9.92 g, 91% yield). 1H NMR (400 MHz, d6-DMSO) δ 0.95 (s, 3H), 8.22 (s, 1H).

Workup

  1. temperatureThe flask was cooled
  2. customThe volatiles were removed in vacuo
  3. extractionAfter extracting into CH2Cl2 (×3)
  4. washthe combined organic layers were washed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a5176a9088124df6b1037b927b862831
Source dataset
uspto-grants-2014_11
Patent number
US08889695B2

Reaction notes

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