2,2-Dimethoxypropane → (2,2-Dimethyl-1,3-dioxan-5-yl)methanol

HRID 1874788Notes

Reaction equation

HRID 1874788 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].CO[C:10](OC)([CH3:12])[CH3:11].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1COCC1>[CH3:11][C:10]1([CH3:12])[O:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2][O:1]1

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 78432TrimethylolmethaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Hydroxymethyl)-1,3-propanediol (1.0 g, 9.4 mmol), 2,2-bis(methyloxy)propane (2.3 mL, 18.8 mmol) and p-toluenesulfonic acid monohydrate (0.09 g, 0.5 mmol) were dissolved in THF and stirred for ˜60 h. To the solution was added triethyl amine (1.0 mL) and the solvent was evaporated. Purification was accomplished by column chromatography (CH2Cl2:MeOH) to afford the title compound (0.6 g, 44%) as a oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 4.52 (t, 1H), 3.80 (dd, 2H), 3.59 (dd, 2H), 3.36 (dd, 2H), 1.63-1.72 (m, 1H), 1.28 (d, 6H).

Workup

  1. customthe solvent was evaporated
  2. customPurification

Sources & evidence

ORD record
ord-450f7f2a5c864964a8f0b359dcff027d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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