4-Hydroxybenzaldehyde → HCID 86669850, compound

HRID 1484088Notes

Reaction equation

HRID 1484088 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH2:34][OH:35])[CH:31]=[CH:32][CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C:51]1[CH:58]=[CH:57][C:54]([CH:55]=[O:56])=[CH:53][CH:52]=1>C1COCC1>[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:31]=[CH:32][CH:33]=1)[CH2:34][O:35][C:51]1[CH:58]=[CH:57][C:54]([CH:55]=[O:56])=[CH:53][CH:52]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 743413-(Phenylmethoxy)benzenemethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 86669850HCID 86669850, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of triphenylphosphine (1.1 mmols) in THF (2 mLs) was added 34 (1.1 mmols). The solution was immediately cooled to 0° C. and diisopropyl azodicarboxylate (1.1 mmols) was added dropwise and the mixture was stirred at this low temperature for 15 minutes. After this time, 4-hydroxybenzaldehyde (1 mmol) was added to the reaction vessel, still stirring at 0° C. The mixture was warmed slowly to ambient temperature and stirred for 15 hours. At this time, the THF was evaporated, reconstituted in Et2O and filtered through a small portion of silica gel. The eluent was collected and evaporated to dryness. The title product (0.45 mmols) was recovered after flash chromatography. 1H NMR (300 MHz, CDCl3) δ 9.89 (s, 1H), 7.91-7.77 (m, 2H), 7.50-7.30 (m, 6H), 7.03 (ddd, J=5.1, 11.5, 24.0, 5H), 5.13 (s, 2H), 5.08 (s, 2H). 13C NMR (75 MHz, CDCl3) δ 191.04, 163.88, 159.36, 137.82, 136.98, 132.24, 130.09, 128.86, 128.29, 127.74, 120.05, 115.39, 114.79, 114.14, 77.70, 77.27, 76.85, 70.25.

Workup

  1. stirringstill stirring at 0° C
  2. temperatureThe mixture was warmed slowly to ambient temperature
  3. stirringstirred for 15 hours
  4. customAt this time, the THF was evaporated
  5. filtrationfiltered through a small portion of silica gel
  6. customThe eluent was collected
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-08b0cd5af1994d03ba7df3d69c7f6ed0
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

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