4-Hydroxybenzaldehyde → HCID 178444466, compound

HRID 2371351Notes

Reaction equation

HRID 2371351 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14][OH:15])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].O[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14][O:15][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178444473HCID 178444473, compound

Product 1

HCID 178444466HCID 178444466, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.0 g of (E)-3-(trans-4-pentylcyclohexyl)allyl alcohol, 2.9 g of 4-hydroxybenzaldehyde, 4.1 g of diethyl azodicarboxylate, 6.2 g of triphenylphosphine and 100 ml of tetrahydrofuran was stirred at room temperature overnight and then concentrated. The residue was suspended in 300 ml of hexane, filtered and again concentrated. Chromatography of the residue on silica gel with toluene and recrystallization from hexane gave 4.5 g of pure 4-[(E)-3-(trans-4-pentylcyclohexyl)allyloxy]benzaldehyde with m.p. 55° C.

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. concentrationagain concentrated
  4. customChromatography of the residue on silica gel with toluene and recrystallization from hexane

Sources & evidence

ORD record
ord-72124c6a43934d83b41b85ec7af9fde9
Source dataset
uspto-grants-1992_03
Patent number
US05093027

Reaction notes

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