4-Chlororesorcinol → 4-Methoxyphenylacetaldehyde

HRID 1867565Notes

Reaction equation

HRID 1867565 reaction equation
ClC1C=CC(O)=CC=1O.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](O)=[O:20])=[CH:14][CH:13]=1.CC([O-])=O.[Na+]>B(F)(F)F>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]=[O:20])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 17314-ChlororesorcinolHCID 76904-Methoxyphenylacetic AcidHCID 517045Sodium Acetate

Product 1

HCID 797824-Methoxyphenylacetaldehyde

Reagents, catalysts & solvents 1

HCID 6356Boron trifluorideSolvent

Conditions

Temperature
90 °C

Procedure

4-Chlororesorcinol (1 eq) and para-methoxyphenylacetic acid (1 eq) were combined in boron trifluoride diethyletherate (5 eq) and heated to 90° C. under nitrogen for 3 hours. The reaction was allowed to cool to room temperature and was then added drop wise to 10% NaOAc (aq). The mixture was allowed to stand overnight, and the subsequent solid was collected by vacuum filtration. The solid was dried under vacuum to give 1-5-chloro-2,4-dihydroxy-phenyl)-2-(4-methoxy-phenyl)-ethanone.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe subsequent solid was collected by vacuum filtration
  3. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-e37a55f7e2084c6a805533afac66f96e
Source dataset
uspto-grants-2009_12
Patent number
US07632855B2

Reaction notes

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