Toluene → HCID 68114824, compound

HRID 247697

Reaction equation

HRID 247697 reaction equation
[CH2:1]([CH:6]([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:11]([O:15][C:16]1[CH:23]=[CH:22][C:19](C=O)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH3:14].[C:24]1(C)C=CC=CC=1>S(=O)(=O)(O)O>[CH2:11]([O:15][C:16]1[CH:23]=[CH:22][C:19]([C@H:7]2[C@H:6]([CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:9][O:10][CH2:24][O:8]2)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 1140TolueneHCID 798134-ButoxybenzaldehydeHCID 110947511,3-Propanediol, 2-(4-pentenyl)-

Product 1

HCID 68114824HCID 68114824, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of 3.6 g of 2-(4-pentenyl)-1,3-propanediol, 4.4 g of p-butoxybenzaldehyde, 75 ml of toluene and 3 drops of 10% sulphuric acid was heated to boiling for 2.5 hours, whereby about 50 ml of wet solvent were distilled off and were replaced by the dropwise addition of 50 ml of fresh toluene. Thereafter, the mixture was neutralized with 4 drops of triethylamine and, after cooling, was extracted twice with 50 ml of 5% sodium hydrogen carbonate solution each time and twice with 50 ml of water each time. The organic phase was dried over sodium sulphate and concentrated. The residue (7.5 g) was chromatographed on silica gel with hexane/ethyl acetate (vol. 92:8), whereby 4.2 g of trans-4-(p-butoxyphenyl)-5-(4-pentenyl)-m-dioxane were obtained. Two-fold recrystallization from hexane gave 2.2 g of pure product with m.p. (C-N) 29.5° C. and cl.p. (N-I) 30.7° C.

Workup

  1. temperaturewas heated
  2. distillationwhereby about 50 ml of wet solvent were distilled off
  3. additionwere replaced by the dropwise addition of 50 ml of fresh toluene
  4. temperatureafter cooling
  5. extractionwas extracted twice with 50 ml of 5% sodium hydrogen carbonate solution each time
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. concentrationconcentrated
  8. customThe residue (7.5 g) was chromatographed on silica gel with hexane/ethyl acetate (vol. 92:8)

Sources & evidence

ORD record
ord-548bcd68c9294176a6facae08e2fe17b
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Linked notes

Loading…