6-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde → 6-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 2052319Notes

Reaction equation

HRID 2052319 reaction equation
[CH:1]([CH:3]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH:4]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=O.[CH3:20][CH:21]([CH2:44][CH2:45][CH2:46][CH3:47])[C:22]([C:24]1C=CC=CC=1P(=C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:23]>O1CCCC1>[OH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:4]1[CH:3]([CH:1]=[CH:24][C:22](=[O:23])[CH:21]([CH3:20])[CH2:44][CH2:45][CH2:46][CH3:47])[CH2:11][CH2:10][C:5]21[O:9][CH2:8][CH2:7][O:6]2

Participants

4

Reactant 2

HCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehydeHCID 867367972-Methylhexanoyl-methylenetriphenylphosphorane

Product 1

HCID 570760486-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonaneYield 101.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (3.88 g.) and 2-methylhexanoyl-methylenetriphenylphosphorane (6.0 g.) in dry tetrahydrofuran (30 ml.) was heated to reflux under nitrogen for 18 hours. The solvent was removed in vacuo and the residue triturated with petroleum ether (b.p. 60°-80° C.), allowed to stand at 0° C., filtered to remove triphenylphosphine oxide and the filtrate evaporated to give 6-(7-hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane (5.56 g), νmax 1620 cm-1, 1660 cm-1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated with petroleum ether (b.p. 60°-80° C.)
  5. customto stand at 0° C.
  6. filtrationfiltered
  7. customto remove triphenylphosphine oxide
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-32c3c405d3a74bcb8357d2b1f5742763
Source dataset
uspto-grants-1980_01
Patent number
US04183870

Reaction notes

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