4-Hydroxybenzaldehyde → Methyl 2-(4-formylphenoxy)acetate

HRID 986555Notes

Reaction equation

HRID 986555 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:11][C:10]([O:14][CH3:15])=[O:13])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 66774Methyl GlycolateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 758214Methyl 2-(4-formylphenoxy)acetateYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-hydroxy benzaldehyde, (1.22 g, 0.01 m), methyl glycolate (0.97 g, 0.01 m), and triphenylphosphine, (3.93 g, 0.015 m), in dry tetrahydrofuran, (50 ml) was stirred with cooling in ice and diethylazodicarboxylate, (2.61 g, 0.015 m), added dropwise. The solution was stirred at room temperature for 0.5 hours, then evaporated in vacuo to dryness. Column chromatography of the residue on silica gel eluting with chloroform yielded 1.30 g (67%) of the title compound as an oil which crystallized on standing, mp 39°-41° C., νmax (mull) 1750, 1680, 1595, 1575, 1505 cm-1.

Workup

  1. temperaturewith cooling in ice
  2. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-58f506e938fb4a22b96ab28274efd451
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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