Neopentyl glycol → 2-(4-Benzyloxy-3-propoxyphenyl)-5,5-dimethyl-1,3-dioxane

HRID 987868Notes

Reaction equation

HRID 987868 reaction equation
[CH3:1][C:2]([CH2:6][OH:7])([CH2:4][OH:5])[CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][C:29]=1[O:36][CH2:37][CH2:38][CH3:39])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH2:20]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]2[O:7][CH2:6][C:2]([CH3:3])([CH3:1])[CH2:4][O:5]2)=[CH:30][C:29]=1[O:36][CH2:37][CH2:38][CH3:39])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 31344Neopentyl glycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 229870904-Benzyloxy-3-propoxybenzaldehyde

Product 1

HCID 229870842-(4-Benzyloxy-3-propoxyphenyl)-5,5-dimethyl-1,3-dioxaneYield 64.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.45 g (13.9 mmol) of neopentylglycol and 88 mg (0.46 mmol) of p-toluenesulfonic acid monohydrate were added to a solution of 1.25 g (4.63 mmol) of 4-benzyloxy-3-propoxybenzaldehyde in 50 ml of toluene and then refluxed for 1 hour under a water separator. Thereafter, the reaction mixture was cooled to room temperature and partitioned between toluene and a saturated sodium bicarbonate solution, and the organic phase was washed several times with water, dried over magnesium sulfate, filtered and evaporated down. Crystallization of the residue from 10 ml of diethyl ether gave 1.07 g of 2-(4-benzyloxy-3-propoxyphenyl)-5,5-dimethyl-1,3-dioxane.

Workup

  1. temperaturerefluxed for 1 hour under a water separator
  2. custompartitioned between toluene
  3. washa saturated sodium bicarbonate solution, and the organic phase was washed several times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated down
  7. customCrystallization of the residue from 10 ml of diethyl ether

Sources & evidence

ORD record
ord-9c85a1abfe0f453183a73acca23d2827
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

Loading…