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

HRID 1666231Notes

Reaction equation

HRID 1666231 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.CCN(CC)CC>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)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-hydroxymethylpropane-1,3-diol (200 mg) in THF (1 ml) was added 2,2-dimethoxypropane (0.278 ml) and p-toluenesulfonic acid monohydrate (11 mg). The mixture was stirred at RT for 4 h. NEt3 (262 μl) was added and the mixture was stirred for further 15 min. The solvent was removed and the residue was purified by CC (DCM to DCM/MeOH 95/5) to afford 220 mg of the desired compound.

Workup

  1. stirringthe mixture was stirred for further 15 min
  2. customThe solvent was removed
  3. customthe residue was purified by CC (DCM to DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-f7db469dfc0547838bb3631d4b287bb2
Source dataset
uspto-grants-2011_10
Patent number
US08044055B2

Reaction notes

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