Hydroxyphenylacetic acid → HCID 15126650, compound

HRID 2280222Notes

Reaction equation

HRID 2280222 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=1.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:18](=[O:19])[CH2:17][C:14]1[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 8000Boron trifluoride etherateHCID 118432-Methylresorcinol

Product 1

HCID 15126650HCID 15126650, compound

Conditions

Temperature
110 °C

Procedure

2-Methylresorcinol (4.00 g, 1 equivalent) and 4-Hydroxyphenylacetic acid (5.00 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 BF3.OEt2 (20 ml, 5 equiv.) was added to the mixture while stirring. The mixture was refluxed (110° C.). A yellow solid formed at 20 minutes indicating that the reaction had gone to completion. The reaction was left on heat for a further 10 minutes and then 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-(4-hydroxy-phenyl)-ethanone in >95% purity. The solid was dried on a freeze dryer for 24 hours (8.93 g, 99%).

Workup

  1. customThe round bottom flask was attached to a condenser
  2. customplaced in an oil bath
  3. customA yellow solid formed at 20 minutes
  4. waitThe reaction was left
  5. temperatureon heat for a further 10 minutes
  6. temperaturecooled to room temperature
  7. filtrationThe yellow solid was collected by suction filtration
  8. washwashed with distilled water (200 ml)
  9. customto remove any excess BF3.OEt2 present
  10. customThe solid was dried on a freeze dryer for 24 hours (8.93 g, 99%)

Sources & evidence

ORD record
ord-c494707b303e4e85a3909e509c3556ef
Source dataset
uspto-grants-2015_09
Patent number
US09138478B2

Reaction notes

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