Water → HCID 54117239, compound

HRID 1871659Notes

Reaction equation

HRID 1871659 reaction equation
O.[OH:2][CH2:3][C:4]12[O:11][CH:7]([CH2:8][CH:9]1[CH3:10])[CH2:6][C:5]2([CH3:13])[CH3:12]>C(O)C>[CH:3]([C:4]12[O:11][C@H:7]([CH2:8][C@H:9]1[CH3:10])[CH2:6][C:5]2([CH3:12])[CH3:13])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 18692718HCID 18692718, compound

Product 1

HCID 54117239HCID 54117239, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Workup: The reaction mixture obtained as in Example 1a was mixed with 200 ml of water at RT, the upper phase was separated off, and the aqueous phase was extracted three times with 150 ml of hexane each time. The organic phases were combined, washed twice with 150 ml of water and evaporated (rotary evaporator). The residue of 25.5 g was distilled to result in 22.1 g of 1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane with a boiling point of 54-61° C. under 1.5 mbar, which is 90% pure according to gas chromatography (GC), (equivalent to a yield of 85% of theory). A byproduct was ascertained to be 1-hydroxymethyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane (about 4% of theory). The structure of the product was evident for example from the 1H-NMR spectrum: 250 MHz, (C6D6), δ=1.09 (d, J=8 Hz, 3 H), 4.16 (t, J=6 Hz, 1 H), 9.94 (s, 1 H); [α]D25 =-20.7 (c=1, ethanol).

Workup

  1. customWorkup: The reaction mixture obtained as in Example 1a
  2. customthe upper phase was separated off
  3. extractionthe aqueous phase was extracted three times with 150 ml of hexane each time
  4. washwashed twice with 150 ml of water
  5. customevaporated
  6. custom(rotary evaporator)
  7. distillationThe residue of 25.5 g was distilled
  8. customto result in 22.1 g of 1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane with a boiling point of 54-61° C. under 1.5 mbar, which

Sources & evidence

ORD record
ord-3dbb98ad746c4abf98c440a15ba32b72
Source dataset
uspto-grants-2000_08
Patent number
US06103940

Reaction notes

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