(3,4-Dimethoxyphenyl)acetic acid → HCID 21270136, compound

HRID 661591Notes

Reaction equation

HRID 661591 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:20][C:21](O)=[O:22])[CH:15]=[CH:16][C:17]=1[O:18][CH3:19].B(F)(F)F.CCOCC>>[OH:4][C:3]1[C:2]([CH3:1])=[C:8]([OH:9])[CH:7]=[CH:6][C:5]=1[C:21](=[O:22])[CH2:20][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:12]([O:11][CH3:10])[CH:13]=1

Participants

4

Reactant 3

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 8000Boron trifluoride etherate2×HCID 118432-Methylresorcinol

Product 1

HCID 21270136HCID 21270136, compound

Conditions

Temperature
110 °C

Procedure

2-Methylresorcinol (6.285 g, 1 equivalent) and 3,4-dimethoxyphenylacetic acid (9.251 g, 1 equivalent) were added to a round bottom flask. The round bottom flask was attached to a condenser and placed in an oil bath, the whole system was kept under nitrogen. Distilled boron trifluoride diethyl etherate, BF3.OEt2 (42 ml, 5 equiv.) was added to the mixture while stirring. The mixture was refluxed (110° C.). A yellow solid formed at 75 minutes indicating that the reaction had gone to completion. The reaction was heated for a further 10 minutes and cooled to room temperature. The yellow solid was collected by suction filtration and washed with distilled water (200 ml) to remove any excess BF3.OEt2 present. 1H NMR in d-DMSO indicated the yellow solid was 1-(2,4-dihydroxy-3-methyl-phenyl)-2-(3,4-dimethoxy-phenyl) ethanone in >95% purity. The solid was dried on a freeze dryer for 24 hours (6.303 g, 43%).

Workup

  1. customThe round bottom flask was attached to a condenser
  2. customplaced in an oil bath
  3. customA yellow solid formed at 75 minutes
  4. temperatureThe reaction was heated for a further 10 minutes
  5. temperaturecooled to room temperature
  6. filtrationThe yellow solid was collected by suction filtration
  7. washwashed with distilled water (200 ml)
  8. customto remove any excess BF3.OEt2 present
  9. customThe solid was dried on a freeze dryer for 24 hours (6.303 g, 43%)

Sources & evidence

ORD record
ord-90913d47ec3b40178c048db2b66e4b45
Source dataset
uspto-grants-2011_12
Patent number
US08084628B2

Reaction notes

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