4-Hydroxybenzaldehyde → 4-[(2,6-dichlorobenzyl)oxy]benzaldehyde

HRID 2268734Notes

Reaction equation

HRID 2268734 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 301591-Bromomethyl-2,6-dichlorobenzene

Product 1

HCID 7354664-[(2,6-dichlorobenzyl)oxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-hydroxybenzaldehyde (19.2 g, 157.5 mmol), 2,6-dichlorobenzylbromide (36 g, 150 mmol) and potassium carbonate (22.77 g, 165 mmol) in DMF (150 ml) was stirred at room temperature overnight. The mixture was filtered and the filtrate evaporated under reduced pressure. The residue was dissolved in ether (500 ml), and washed with aqueous NaOH (5%, 100 ml), water (100 ml) and brine (100 ml), dried (Na2SO4) and evaporated under reduced pressure. The orange crystalline solid obtained was recrystallised from diisopropylether to give the title compound as slightly orange needles (35.8 g, 85%), m.p. 70-71°. δH (CDCl3) 9.91 (1H, s, CHO), 7.87 (2H, d, J 8.9 Hz, ArH), 7.40-7.24 (3H, m, ArCl2H), 7.12 (2H, d, J 8.7 Hz, ArH) and 5.36 (2H, s, ArCH2OAr); m/z (ESI, 60V) 281 (M++1); Found: C, 59.76; H, 3.57. C14H10O2Cl2 requires C, 59.81; H, 3.59%.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ether (500 ml)
  4. washwashed with aqueous NaOH (5%, 100 ml), water (100 ml) and brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe orange crystalline solid obtained
  8. customwas recrystallised from diisopropylether

Sources & evidence

ORD record
ord-ff4899894a5d4f8e92478e2f2d719978
Source dataset
uspto-grants-2001_12
Patent number
US06329362B1

Reaction notes

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