4-Hydroxybenzaldehyde → HCID 21703917, compound

HRID 475518Notes

Reaction equation

HRID 475518 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][OH:7])([CH3:3])[CH3:2].O[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1>N(C(OCC)=O)=NC(OCC)=O>[CH:1]([O:4][CH2:5][CH2:6][O:7][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1264-Hydroxybenzaldehyde2×HCID 7996Isopropylethanediol2×HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine

Product 1

HCID 21703917HCID 21703917, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 220568ethyl N-ethoxycarbonyliminocarbamateSolvent

Procedure

To a solution of 2-isopropoxyethanol (600 mg, 5.76 mmol), p-hydroxybenzaldehyde (0.78 g, 6.34 mM) and triphenylphosphine in THF (20 ml) (1.6 g, 6.1 mmol), diethyl azodicarboxylate (40% in toluene) was added at 0° C. over 10 minutes while stirring. Then, the mixture was stirred at room temperature for 18 hours until the initial reaction product of 2-isopropoxyethanol and p-hydroxybenzaldehyde disappeared. The resulting solution was concentrated and purified by silica gel chromatography (hexane:ethylacetate=5:1) to obtain 4-(2-isopropoxyethoxy)benzaldehyde as yellow oil (0.98 g, yield: 82%).

Workup

  1. stirringThen, the mixture was stirred at room temperature for 18 hours until the initial
  2. concentrationThe resulting solution was concentrated
  3. custompurified by silica gel chromatography (hexane:ethylacetate=5:1)

Sources & evidence

ORD record
ord-e5566eeb670641dfad8a422c6064d339
Source dataset
uspto-grants-2014_01
Patent number
US08637558B2

Reaction notes

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