3-Hydroxybenzaldehyde → 3-(4-Methoxyphenoxy)benzaldehyde

HRID 1393345Notes

Reaction equation

HRID 1393345 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C(Cl)Cl.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 8471TriethylamineHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 1235533-(4-Methoxyphenoxy)benzaldehydeYield 19%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (7.1 ml, 51 mmol) was added dropwise at room temperature to a suspension of 3-hydroxybenzaldehyde (1.72 g, 14.1 mmol), 4-methoxyphenylboronic acid (3.16 g, 20.8 mmol), molecular sieves 4A powder (1.95 g) and copper (II) acetate (2.96 g, 16.3 mmol) in methylene chloride (100 ml), and the mixture was stirred for 27.5 hrs. The reaction mixture was diluted with ethyl acetate (200 ml), and the insoluble materials were filtered off and washed with ethyl acetate. The filtrate and washings were combined, washed with 10% hydrochloric acid and brine in turn and dried. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7) to give 3-[(4-methoxy)phenoxy]benzaldehyde (596 mg, 19%) as a pale brown oil.

Workup

  1. filtrationthe insoluble materials were filtered off
  2. washwashed with ethyl acetate
  3. washwashed with 10% hydrochloric acid and brine in turn
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7)

Sources & evidence

ORD record
ord-705ef7571d274f3d82b97c1ae516b5f0
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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