4-Hydroxybenzaldehyde → HCID 23050521, compound

HRID 1651790Notes

Reaction equation

HRID 1651790 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[CH:9])[CH3:5])[CH3:2].C([Li])CCC.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[C:9][CH:20]([C:19]1[CH:22]=[CH:23][C:16]([OH:15])=[CH:17][CH:18]=1)[OH:21])[CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 25517Ammonium ChlorideHCID 867741-Propyne, 3-(1-ethoxyethoxy)-HCID 178418339Butyllithium

Product 1

HCID 23050521HCID 23050521, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 16 g (124.8 mmol) of 1-(1-ethoxyethoxy)-2-propyne in 270 ml of tetrahydrofuran was treated at -78° under argon with 78 ml of n-butyllithium (1.6 M in hexane). The mixture was stirred at -40° for 30 minutes and then a solution 7.62 g (62.4 mmol) of 4-hydroxybenzaldehyde in 53 ml of tetrahydrofuran was added within 10 minutes. The reaction mixture was warmed to 0°, stirred at 0° for a further 1 hour and then treated with 100 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed in succession with saturated sodium chloride solution and with water, dried over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 600 g of silica gel (elution agent ether/hexane 1:1). There was obtained 4-(1-ethoxyethoxy)-(4-hydroxyphenyl)-2-butyn-1-ol as an oil.

Workup

  1. temperatureThe reaction mixture was warmed to 0°
  2. stirringstirred at 0° for a further 1 hour
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. washThe combined organic phases were washed in succession with saturated sodium chloride solution and with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on 600 g of silica gel (elution agent ether/hexane 1:1)

Sources & evidence

ORD record
ord-5fb2dee539de4ff1ab38e274bd3ffb71
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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