Dichloromethane → HCID 19967040, compound

HRID 976254Notes

Reaction equation

HRID 976254 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:15](Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:15]1[O:12][C:11]2[C:2](=[C:3]([CH:8]=[CH:9][C:10]=2[O:13][CH3:14])[C:4]([O:6][CH3:7])=[O:5])[O:1]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 11694090Methyl 2,3-dihydroxy-4-methoxybenzoate

Product 1

HCID 19967040HCID 19967040, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

Compound 121 (16.12 g, 0.081 mol) was dissolved in 500 mL of DMF. Then 100 mL of methylene chloride and 26 g (0.464 mol) of potassium carbonate were added. The mixture was heated to 105° C. with vigorous stirring for 6 hours. The potassium carbonate was filtered and the DMF was removed in vacuo. The residue was poured into ice-water and let stand overnight. The precipitated product 122 was filtered and washed with water until neutral. The dried gray white solid weighed 15.60 g (yield 91%) and was recrystallized from methanol as brilliant long needles, m.p. 122°-124° C. IR cm-1 1710 (ester C=O); 1H NMR δ ppm 3.90 (s, 3H, OCH3), 3.95 (s, 3H, ArOCH3), 6.11 (s, 2H, OCH2O), 6.57 and 7.45 (each d, J=9 Hz, 1H, ArH). Anal. (C10H10O5)C, H.

Workup

  1. filtrationThe potassium carbonate was filtered
  2. customthe DMF was removed in vacuo
  3. additionThe residue was poured into ice-water
  4. waitlet stand overnight
  5. filtrationThe precipitated product 122 was filtered
  6. washwashed with water until neutral
  7. customwas recrystallized from methanol as brilliant long needles, m.p. 122°-124° C

Sources & evidence

ORD record
ord-7b6f5bab6a9c4715a68d4e2421845d9c
Source dataset
uspto-grants-1997_03
Patent number
US05612341

Reaction notes

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