Styrene Oxide → HCID 20133241, compound

HRID 845005Notes

Reaction equation

HRID 845005 reaction equation
C1(C)C=CC(S(O[CH:11]([C:22]2[CH2:23][O:24][CH:25]=CC=2)[CH2:12][CH2:13][CH:14](CO)CCCCC)(=O)=O)=CC=1.[CH2:29]1[O:37][CH:30]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O)C(O)CCCCC>CN(P(N(C)C)(N(C)C)=O)C>[C:31]1([CH:30]2[CH2:25][O:24][CH:23]([CH2:22][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:29][O:37]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 7276Styrene OxideHCID 773021,2-HeptanediolHCID 131715623HCID 131715623, compound

Product 1

HCID 20133241HCID 20133241, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 4.06 g. 4-hydroxymethyl-3-oxa-1-phenyl-nonan-1-ol 1-mono-p-toluene sulphonate (obtainable by reaction of styrene oxide with heptane-1,2-diol and partial tosylation of the 4-hydroxymethyl-3-oxa-1-phenylnonan-1-ols obtained) in 100 ml. phosphoric acid hexamethyltriamide is heated for 24 hours to 80°. One evaporates, works up as usual and obtains 2-phenyl-5-pentyl-1,4-dioxane as an oily isomer mixture. Isomerization of 1 g. of the mixture by 2 hours heating with 0.05 g. K tert.-butylate in 10 ml. dimethyl sulphoxide to 80° leads to trans-2-phenyl-5-pentyl-1,4-dioxane.

Workup

  1. customobtained) in 100 ml
  2. customOne evaporates

Sources & evidence

ORD record
ord-b7bb5a7a322a43f287457be4f214c864
Source dataset
uspto-grants-1988_07
Patent number
US04755323

Reaction notes

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