3-Hydroxybenzaldehyde → 3-(2-Methylthioethoxy)benzaldehyde

HRID 1669347Notes

Reaction equation

HRID 1669347 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][S:30][CH2:31][CH2:32]O.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:29][S:30][CH2:31][CH2:32][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 789252-(Methylthio)ethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 231317123-(2-Methylthioethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1.00 g of 3-hydroxybenzaldehyde, 25 ml of tetrahydrofuran, 2.40 g of triphenylphosphine and 0.78 ml of 2-methylthioethanol was added dropwise 3.50 ml of diethyl azodicarboxylate (40% toluene solution), and the mixture was stirred at room temperature for 15.5 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 0.71 g of oily 3-(2-methylthioethoxy)benzaldehyde [Compound No. (f)].

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-141283796d95413894d3aac284a2143c
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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