Sodium borohydride → 7,12-Dioxaspiro[5.6]dodecane-9-methanol

HRID 344003Notes

Reaction equation

HRID 344003 reaction equation
[CH:1]([CH:3]1[CH2:14][CH2:13][O:12][C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[O:5][CH2:4]1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][CH:3]1[CH2:14][CH2:13][O:12][C:6]2([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[O:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109545329-Formyl-7,12-dioxaspiro[5,6]dodecane

Product 1

HCID 110308447,12-Dioxaspiro[5.6]dodecane-9-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 9-formyl-7,12-dioxaspiro[5,6]dodecane of formula IV (5 g) in methanol (15 ml) was added in small portions NaBH4 (0.5 g) while stirring the solution and maintaining the temperature at 10° C. After complete addition, the reaction mixture was stirred for 3 hr at 20° C. The product residue obtained after evaporation of methanol was treated with water (20 ml), extracted into ether and dried over K2CO3. Evaporation of ether gave 9-hydroxymethyl-7, 12-dioxaspiro[5,6]dodecane of formula V (5 g) of the drawings as colorless viscous liquid.

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred for 3 hr at 20° C
  3. customThe product residue obtained
  4. customafter evaporation of methanol
  5. additionwas treated with water (20 ml)
  6. extractionextracted into ether
  7. dry with materialdried over K2CO3
  8. customEvaporation of ether

Sources & evidence

ORD record
ord-a0d0b297fd33460b9a94c5ee67e5c3df
Source dataset
uspto-grants-1999_01
Patent number
US05864046

Reaction notes

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