Water → (9-Hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-acetaldehyde

HRID 1615117Notes

Reaction equation

HRID 1615117 reaction equation
O.[OH:2][C:3]1([CH2:16][CH:17]([OH:20])CO)[CH2:15][CH2:14][C:6]2([O:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][O:7]2)[CH2:5][CH2:4]1>ClCCl>[OH:2][C:3]1([CH2:16][CH:17]=[O:20])[CH2:15][CH2:14][C:6]2([O:7][CH2:8][C:9]([CH3:12])([CH3:13])[CH2:10][O:11]2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 962WaterHCID 679957253-(9-Hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-propane-1,2-diol

Product 1

HCID 86668369(9-Hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Water (7 mL) and NalO4 (5.41 g) are added to a solution of 3-(9-hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-propane-1,2-diol (4.63 g) in dichloromethane (70 mL) chilled in an ice bath. The cooling bath is removed and the resulting mixture is vigorously stirred at room temperature overnight. The mixture is then filtered and the filtrate is dried (Na2SO4) and concentrated to give the crude title compound that is directly subjected to the next reaction step. Yield: 4.28 g (crude); Mass spectrum (ESI+): m/z=243 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. filtrationThe mixture is then filtered
  4. dry with materialthe filtrate is dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d65bb656f2d34e909c8d8f661618e459
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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