Triethylamine → (2,2,5,5-Tetramethyl-1,3-dioxolan-4-yl)methanol

HRID 1589124Notes

Reaction equation

HRID 1589124 reaction equation
[CH3:1][C:2]([OH:8])([CH3:7])[CH:3]([OH:6])[CH2:4][OH:5].C(N(CC)CC)C.[O-2].[Al+3].[O-2].[O-2].[Al+3].[CH3:21][C:22](C)([CH:24]1COC(C)(C)O1)O>CC(C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)Cl>[CH3:21][C:22]1([CH3:24])[O:6][CH:3]([CH2:4][OH:5])[C:2]([CH3:7])([CH3:1])[O:8]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9989226AluminaHCID 13044593HCID 13044593, compoundHCID 130445963-Methylbutane-1,2,3-triol

Product 1

HCID 13227508(2,2,5,5-Tetramethyl-1,3-dioxolan-4-yl)methanolYield 64.2%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 g of (RS)-3-methyl-1,2,3-butanetriol in 20 ml of acetone is treated with 0.010 g of anhydrous p-toluenesulphonic acid and left at room temperature for 5 days. After the addition of 0.3 ml of triethylamine, the mixture is evaporated at 30°/11 Torr and the residue is distilled at 130°/11 Torr. The distillate (1.55 g) gives, after chromatography on 90 g of neutral aluminium oxide (activity III) with methylene chloride, as the non-polar fraction 0.81 g of (RS)-α,α,2,2-tetramethyl-1,3-dioxolane-4-methanol and as the polar fraction 0.52 g of the desired product.

Workup

  1. customthe mixture is evaporated at 30°/11 Torr
  2. distillationthe residue is distilled at 130°/11 Torr
  3. customThe distillate (1.55 g) gives

Sources & evidence

ORD record
ord-4097af55b6114e7dbb139c26285d97be
Source dataset
uspto-grants-1986_02
Patent number
US04568491

Reaction notes

Loading…