3-Hydroxybenzaldehyde → HCID 15050018, compound

HRID 1421937Notes

Reaction equation

HRID 1421937 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10]1([C:16]2[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:16]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=[CH:18][C:19]([CH2:20][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 154634-Phenylbenzyl chloride

Product 1

HCID 15050018HCID 15050018, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-hydroxybenzaldehyde (6.02 g, 49 mmol), 4-phenyl-benzylchloride (10 g, 49 mmol) and potassium carbonate (20 g, 148 mmol) in N,N'-dimethylformamide (100 ml) was stirred at room temperature for 16 h. The mixture was poured into water (500 ml) and stirred for 1 h. The solid formed was filtered off, washed with water (2×200 ml) and heptane (2×75 ml) and dried in vacuo at 50° C. for 16 h affording 12.3 g (87%) of 3-(biphenyl-4-ylmetoxy)benzaldehyde as a solid. TLC showed presence of unchanged 4-phenylbenzylchloride.

Workup

  1. stirringstirred for 1 h
  2. customThe solid formed
  3. filtrationwas filtered off
  4. washwashed with water (2×200 ml) and heptane (2×75 ml)
  5. customdried in vacuo at 50° C. for 16 h

Sources & evidence

ORD record
ord-c06020895f074ba8b8e42825ce813856
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Reaction notes

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