2-Methyl-1,6-dioxaspiro[4.4]nonane-2-carbaldehyde → (2-Methyl-1,6-dioxaspiro[4.4]nonan-2-yl)methanol

HRID 647754Notes

Reaction equation

HRID 647754 reaction equation
[CH3:1][C:2]1([CH:11]=[O:12])[CH2:6][CH2:5][C:4]2([CH2:10][CH2:9][CH2:8][O:7]2)[O:3]1>O1CCCC1>[CH3:1][C:2]1([CH2:11][OH:12])[CH2:6][CH2:5][C:4]2([CH2:10][CH2:9][CH2:8][O:7]2)[O:3]1

Participants

3

Reactant 1

HCID 132371812-Methyl-1,6-dioxaspiro[4.4]nonane-2-carbaldehyde

Product 1

HCID 13237169(2-Methyl-1,6-dioxaspiro[4.4]nonan-2-yl)methanolYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.70 g of 2-methyl-1,6-dioxaspiro[4.4]nonane-2-carboxaldehyde in tetrahydrofuran was hydrogenated at 60 p.s.i. and 20° C. for 5 hours in the presence of 1.0 g triethylamine promoter and Raney nickel, that had been rinsed in tetrahydrofuran. When all of the starting material had disappeared, the mixture was treated with magnesium sulfate and filtered. Distillation of the filtrate gave 1.43 g of the desired product as a colorless liquid, b.p. 65°-70° C. (1 torr.).

Workup

  1. washand 20° C. for 5 hours in the presence of 1.0 g triethylamine promoter and Raney nickel, that had been rinsed in tetrahydrofuran
  2. additionthe mixture was treated with magnesium sulfate
  3. filtrationfiltered
  4. distillationDistillation of the filtrate

Sources & evidence

ORD record
ord-c6cbff53a17447c4b2e97852d06bf064
Source dataset
uspto-grants-1983_10
Patent number
US04410354

Reaction notes

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