4-Methoxyphenylacetic Acid → HCID 58913540, compound

HRID 1296950Notes

Reaction equation

HRID 1296950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[C:3]=1[OH:10].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=[O:21])=[CH:15][CH:14]=1.B(F)(F)F.CCOCC>>[Cl:1][C:2]1[C:3]([OH:10])=[C:4]([CH3:9])[C:5]([OH:8])=[C:6]([C:20](=[O:21])[CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 76904-Methoxyphenylacetic AcidHCID 8000Boron trifluoride etherateHCID 112059244-chloro-2-methyl-benzene-1,3-diol

Product 1

HCID 58913540HCID 58913540, compound

Procedure

A solution of 4-chloro-2-methyl-benzene-1,3-diol (1 eq) and p-methoxy phenyl acetic acid (1 eq) in boron trifluoride diethyl etherate (8 eq) was refluxed for 5 h, whilst stirring, under nitrogen. The solution was allowed to cool to room temperature, quenched with 10% NaOAc (aq) and left to stand overnight. The resultant precipitate was filtered, washed with water and dried to give 1-(5-chloro-2,4-dihydroxy-3-methyl-phenyl)-2-(4-methoxy-phenyl)-ethanone as a solid.

Workup

  1. customquenched with 10% NaOAc (aq)
  2. waitleft
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-257d1794d6904ce5820b00ca58c8cc56
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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