4-Hydroxybenzaldehyde → HCID 19375145, compound

HRID 128783Notes

Reaction equation

HRID 128783 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCCCCC>[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14856822HCID 14856822, compound

Product 1

HCID 19375145HCID 19375145, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Mitsunobu coupling is carried out as follows: 4-hydroxybenzaldehyde (0.92 g), 6-(2-naphthyloxy)hexanol (1.83 g), and triphenylphosphine (1.97 g) are dissolved in THF (25 ml) and cooled to 15° . Diethyl azodicarboxylate (1.2 ml) is added dropwise, and the mixture stirred at room temperature for 60 hrs. The reaction mixture is diluted with hexane and filtered to remove solids. The filtrate is concentrated and chromatographed with 25% v/v hexane in dichloromethane to provide 4-[6-(2-naphthyloxy)hexyloxy] benzaldehyde (1.5 g) as a white solid.

Workup

  1. temperaturecooled to 15°
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationThe filtrate is concentrated
  5. customchromatographed with 25% v/v hexane in dichloromethane

Sources & evidence

ORD record
ord-5b5a116cfde048a680331e6fe64d1c19
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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