Water → 2-[(Benzyloxy)methyl]-2-methyl-1,6-dioxaspiro[4.4]nonane

HRID 647755Notes

Reaction equation

HRID 647755 reaction equation
[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.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[CH3:1][C:2]1([CH2:11][O:12][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:6][CH2:5][C:4]2([CH2:10][CH2:9][CH2:8][O:7]2)[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 13237169(2-Methyl-1,6-dioxaspiro[4.4]nonan-2-yl)methanol

Product 1

HCID 132371702-[(Benzyloxy)methyl]-2-methyl-1,6-dioxaspiro[4.4]nonaneYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.70 g of 2-methyl-1,6-dioxaspiro[4.4]nonane-2-methanol in 20 ml of dimethylformamide was treated sequentially with 0.60 g of 60% sodium hydride-mineral oil dispersion at 15°-25° C. for 1 hour and then with 1.71 g of benzyl bromide at 0°-25° C. for 1 hour. The resulting mixture was poured into 150 ml of water and extracted with diethyl ether. The ether extract was washed with water, dried and distilled to yield 1.40 g of the desired product as a colorless liquid, b.p. 105°-110° C. (0.3 torr.).

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. washwas washed with water
  4. customdried
  5. distillationdistilled

Sources & evidence

ORD record
ord-aaaddb28ec9740d89d2086364e6bffbd
Source dataset
uspto-grants-1983_10
Patent number
US04410354

Reaction notes

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