Triethylamine → 4-{[(4-Hydroxyphenyl)thio]methyl}benzaldehyde

HRID 68229Notes

Reaction equation

HRID 68229 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[OH:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCOCC1.O>[OH:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH2:2][C:3]2[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2401474-MercaptophenolHCID 112064214-(Bromomethyl)benzaldehyde

Product 1

HCID 578598234-{[(4-Hydroxyphenyl)thio]methyl}benzaldehydeYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-bromomethylbenzaldehyde (0.3 g, 1.5 mmol) and 4-hydroxythiophenol (0.2 g, 1.5 mmol) in 1,4-dioxane (10 mL) was degassed and treated with triethylamine (0.44 mL, 3.11 mmol). After stirring for 1 day the mixture was diluted with water (20 mL) and extracted with ethyl acetate (2-fold 20 mL). The combined organic extracts were washed with brine and dried (sodium sulphate) and the solvent removed in vacuo. The crude material was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (9:1 changing to 0:1, by volume) to give the title compound as a solid, 62% yield, 220 mg.

Workup

  1. extractionextracted with ethyl acetate (2-fold 20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (sodium sulphate)
  4. customthe solvent removed in vacuo
  5. customThe crude material was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (9:1 changing to 0:1, by volume)

Sources & evidence

ORD record
ord-27e1a94d734546d89f486bedceb60609
Source dataset
uspto-grants-2014_09
Patent number
US08822439B2

Reaction notes

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