Butanal → HCID 178445836, compound

HRID 1378265Notes

Reaction equation

HRID 1378265 reaction equation
[CH:1](/[CH:5]1[CH2:10][O:9][CH:8]([CH2:11][CH2:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])[O:7][CH2:6]1)=[CH:2]\[CH2:3][CH3:4].[CH:18](=O)[CH2:19][CH2:20][CH3:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(N(CC)CC)C>[CH2:19]([C@H:18]1[O:15][CH2:14][C@H:13]([CH2:12][CH2:11][C@H:8]2[O:7][CH2:6][C@H:5](/[CH:1]=[CH:2]/[CH2:3][CH3:4])[CH2:10][O:9]2)[CH2:16][O:17]1)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 261ButanalHCID 521998p-Toluenesulfonic acid monohydrateHCID 22910574HCID 22910574, compound

Product 1

HCID 178445836HCID 178445836, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Conditions

Temperature
68 °C

Procedure

A solution of 1.50 g of (E)-2-[2-(5-but-1-enyl-1,3-dioxan-2-yl)ethyl]-1,3-propanediol and 2 ml of butyraldehyde in 40 ml of benzene was treated with 28.5 mg of p-toluenesulfonic acid monohydrate and stirred at 68° C. for 40 minutes. The reaction mixture was neutralized with a few drops of triethylamine and, after cooling, washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product (2.15 g) was chromatographed on 40 g of silica gel with hexane/ethyl acetate 5% (v/v). 1.40 g of isomer mixture having a 52% trans/trans content were obtained. Two-fold recrystallization from hexane gave 0.41 g of pure (E)-trans-2-propyl-5-[2-(trans-5-but-1-enyl-1,3-dioxan-2-yl)ethyl]-1,3-dioxane, m.p. (C-SB) 42° C., cl.p. (SB -I) 117.8° C.

Workup

  1. temperatureafter cooling
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product (2.15 g) was chromatographed on 40 g of silica gel with hexane/ethyl acetate 5% (v/v)
  6. customwere obtained
  7. customTwo-fold recrystallization from hexane

Sources & evidence

ORD record
ord-d11f9f0752e64bcb95d421f271003f12
Source dataset
uspto-grants-1997_09
Patent number
US05667721

Reaction notes

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