4-Hydroxybenzaldehyde → 4-[2-Hydroxy-2-(3-methoxyphenyl)ethoxy]benzaldehyde

HRID 1404639Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:11][O:10]2)[CH:6]=[CH:7][CH:8]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:10][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 78 °C

Procedure

To a stirring solution of 2-(3-methoxyphenyl)oxirane (5.60 g, 37.0 mmol) in toluene (65 mL) was added 4-hydroxybenzaldehyde (6.80 g, 5.60 mmol), 1M NaOH (65 mL) and PEG4000 (polyethylene glycol, 0.85 g) and the stirring mixture was heated at 78° C. overnight. The reaction mixture was allowed to cool to RT and extracted with EtOAc (2×150 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting light brown oil was chromatographed, eluting with 30-40% EtOAc/hexanes. Fractions containing the higher Rf spot were combined and evaporated in vacuo to give 1.86 g (18%) of the title compound as a clear colorless oil. Fractions containing the lower Rf spot were combined and evaporated in vacuo to give 0.90 g (9%) the regioisomer as a nearly colorless oil.

Workup

temperatureto cool to RT
extractionextracted with EtOAc (2×150 mL)
washThe combined extracts were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe resulting light brown oil was chromatographed
washeluting with 30-40% EtOAc/hexanes
additionFractions containing the higher Rf spot
customevaporated in vacuo

Sources & evidence

ORD record: ord-61ed0e48f6a740f8beacb012fccf0273
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912335B2

Reaction notes

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