Triphenylphosphine → 4-Methoxy-3-(11-phenylundecyloxy)benzaldehyde

HRID 377625Notes

Reaction equation

HRID 377625 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[C:12]1([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 12127IsovanillinHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11651716Benzeneundecanol

Product 1

HCID 193562684-Methoxy-3-(11-phenylundecyloxy)benzaldehydeYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxy-4-methoxybenzaldehyde (2.5 grams), 11-phenylundecylalcohol (4.6 grams) and triphenylphosphine (4.9 grams) in tetrahydrofuran at 0° C. is slowly added diethyl azodicarboxylate (2.9 ml). After stirring for 2 hours at room temperature the mixture is concentrated under reduced pressure and purified by column chromatography on a silica gel column using a 9:1 mixture of hexane and ethyl acetate as eluent to give 2.4 grams of a yellow oil. 1H NMR (CDCl3) δ 1H NMR (CDCl3) δ 0.82-1.89 (m, 18H), 2.35-2.70 (m, 2H), 3.95 (s, 3H), 4.00-4.08 (m, 2H), 6.95-7.45 (m, 8H), 9.84 (s, 1H).

Workup

  1. customat 0° C.
  2. concentrationis concentrated under reduced pressure
  3. custompurified by column chromatography on a silica gel column
  4. additiona 9:1 mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-be117ea987f349ecb83ea6f2c2148759
Source dataset
uspto-grants-2000_02
Patent number
US06028086

Reaction notes

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