Formaldehyde → (5-Ethyl-1,3-dioxan-5-yl)methanol

HRID 2249225Notes

Reaction equation

HRID 2249225 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5])[CH3:2].C=O.O.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:3]1([CH2:8][OH:9])[CH2:6][O:7][CH2:13][O:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6510TrimethylolpropaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 78860(5-Ethyl-1,3-dioxan-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a one-liter three neck flask were placed 405 grams of 2-ethyl-2-hydroxymethyl-1,3-propanediol, 90 grams of paraformaldehyde, 0.9 grams of p-toluene sulfonic acid monohydrate and 150 ml of toluene. The flask was equipped with a Dean-stark trap and a condenser. The reaction mixture was stirred at a bath temperature of 120° C. to 170° C. for three hours. The toluene-water was collected, and after removing the toluene, the crude product was distilled under vacuum at 10-11 mm Hg and 115° C. to 117° C. 410 grams of 5-ethyl-5-hydroxymethyl-1,3-dioxane (EHMDO) were collected. The product was then dried by molecular sieve and had a water content of about 350 ppm. NMR spectra confirmed that EHMDO was obtained.

Workup

  1. customThe flask was equipped with a Dean-stark trap and a condenser
  2. customThe toluene-water was collected
  3. customafter removing the toluene
  4. distillationthe crude product was distilled under vacuum at 10-11 mm Hg and 115° C. to 117° C
  5. custom410 grams of 5-ethyl-5-hydroxymethyl-1,3-dioxane (EHMDO) were collected
  6. customThe product was then dried by molecular sieve
  7. customwas obtained

Sources & evidence

ORD record
ord-69e7626135e3418ca3608fb688a1ae83
Source dataset
uspto-grants-1991_08
Patent number
US05043398

Reaction notes

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