Toluene → HCID 178444586, compound

HRID 1285076Notes

Reaction equation

HRID 1285076 reaction equation
[CH:1](/[CH:6]([CH2:9][OH:10])[CH2:7][OH:8])=[CH:2]\[CH2:3][CH2:4][CH3:5].[CH2:11]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH3:14].C1(C)C=CC=CC=1>S(=O)(=O)(O)O.C(N(CC)CC)C.O>[CH2:11]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:20]2[O:10][CH2:9][C@H:6](/[CH:1]=[CH:2]/[CH2:3][CH2:4][CH3:5])[CH2:7][O:8]2)=[CH:22][CH:23]=1)[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 3

HCID 1140TolueneHCID 798134-ButoxybenzaldehydeHCID 151424932-(1E-pentenyl)-1,3-propanediol

Product 1

HCID 178444586HCID 178444586, compoundYield 23.2%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 8471TriethylamineCatalystHCID 962WaterSolvent

Procedure

A mixture of 1.00 g of 2-(trans-1-pentenyl)-1,3-propanediol, 1.11 g of p-butoxybenzaldehyde, 3 drops of 2N sulphuric acid and 40 ml of toluene was heated to reflux for 2 hours with separation of water. The mixture was subsequently treated with 7 drops of triethylamine, left to cool, washed with 5 ml of saturated sodium hydrogen carbonate solution and three times with 10 ml of water each time, dried over sodium carbonate, filtered and concentrated. The semi-crystalline residue (1.86 g) was chromatographed on silica gel with hexane/diethyl ether (vol. 97:3). The product-containing fractions were pooled (0.99 g) and recrystallized twice from hexane at -25° C. There was obtained 0.44 g of pure trans-2-(p-butoxyphenyl)-5-(trans-1-pentenyl)-m-dioxane; m.p. (C-N) 60.6° C., cl.p. (N-I) 61.9° C.

Workup

  1. temperaturewas heated
  2. waitleft
  3. temperatureto cool
  4. washwashed with 5 ml of saturated sodium hydrogen carbonate solution and three times with 10 ml of water each time
  5. dry with materialdried over sodium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe semi-crystalline residue (1.86 g) was chromatographed on silica gel with hexane/diethyl ether (vol. 97:3)
  9. customrecrystallized twice from hexane at -25° C

Sources & evidence

ORD record
ord-d4c43662e98b45078dcff8bedf866649
Source dataset
uspto-grants-1986_01
Patent number
US04565425

Reaction notes

Loading…