2,2-Dimethoxypropane → 5-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

HRID 1881666Notes

Reaction equation

HRID 1881666 reaction equation
O.[C:2]1([CH3:12])[CH:7]=CC(S(O)(=O)=O)=C[CH:3]=1.[CH3:13][O:14][C:15]([O:18]C)([CH3:17])[CH3:16].O.C1(C)C(S(O)(=O)=[O:28])=CC=CC=1>CC(C)=O>[CH3:16][C:15]1([CH3:17])[O:18][CH2:7][C:2]([CH3:12])([CH2:3][OH:28])[CH2:13][O:14]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 3737095-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Alternative Procedure: 4-Toluenesulfonic acid monohydrate (51.3 g) in acetone (275 mL) was stirred with 2,2-dimethoxy propane (75 mL) and toluenesulfonic acid monohydrate (1.3 g) for 18 hours at room temperature, and worked up in a similar manner as indicated in the procedure above, to afford 52.12 g (76% yield), by 72-75° C./0.65 mmHg. Mass spec: m/z 161 (M++1). Anal Calcd for C8H16O3: C, 59.98; H, 10.07%. Found: C, 59.62; H, 10.07%. 1H NMR (CDCl3) δ ppm: 0.83 (s, 3H), 1.40 (s, 3H), 1.44 (s, 3H), 3.59-3.69 (m, 6H). 13C NMR: 17.69, 20.25, 27.41, 34.86, 65.90, 66.43, 98.1 (7 sp3C).

Workup

  1. customto afford 52.12 g (76% yield)
  2. customby 72-75° C.

Sources & evidence

ORD record
ord-c328636e59364b2d9591a0b9179e7414
Source dataset
uspto-grants-2012_11
Patent number
US08318888B1

Reaction notes

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