Methanol → HCID 86645267, compound

HRID 1255384Notes

Reaction equation

HRID 1255384 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].F[C:11](F)(F)[C:12]([OH:14])=O.[CH2:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18].[CH3:23]O>>[C:20]([O:19][CH2:17][CH2:18][C:11]1[C:12](=[O:14])[O:6][C:5]2[C:7]([CH:23]=1)=[CH:8][C:2]([Cl:1])=[C:3]([OH:9])[CH:4]=2)(=[O:22])[CH3:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 17314-ChlororesorcinolHCID 6422Trifluoroacetic acidHCID 8857Ethyl Acetate

Product 1

HCID 86645267HCID 86645267, compoundYield 46%

Conditions

Temperature
98 °C

Procedure

To a flame-dried 50 mL round-bottom flask is weighed 4-chlororesorcinol (1.44 g, 10 mmole) and diethyl-1,3-acetonedicarboxylate (1.82 mL, 10 mmole) and trifluoroacetic acid (10.0 mL) added. This mixture is heated to reflux (98° C.) in an oil-bath for 18 hours, cooled to room-temperature and poured into ice-water (100 mL) with stirring for 1 hour. The resulting off-white precipitate is filtered and washed with ice-cold water, dried in air and in vacuo overnight to give a yellow crystalline powder (1.29 g, 4.56 mmole, 46%) TLC (irrigant=7:3 ethylacetate:methanol, Rf=0.86).

Workup

  1. customTo a flame-dried 50 mL round-bottom flask is weighed
  2. temperatureThis mixture is heated
  3. temperaturecooled to room-temperature
  4. filtrationThe resulting off-white precipitate is filtered
  5. washwashed with ice-cold water
  6. customdried in air and in vacuo overnight

Sources & evidence

ORD record
ord-5efa938ccc2f4140abcea8571900b790
Source dataset
uspto-grants-2013_06
Patent number
US08460862B2

Reaction notes

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