3,3-DIETHOXY-1-PROPANOL Chemical Properties

Boiling point:

90-93 °C/14 mmHg (lit.)

Density 

0.941 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.421(lit.)

Flash point:

196 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

pka

15.05±0.10(Predicted)

color 

Clear colorless

InChI

InChI=1S/C7H16O3/c1-3-9-7(5-6-8)10-4-2/h7-8H,3-6H2,1-2H3

InChIKey

ASERXEZXVIJBRO-UHFFFAOYSA-N

SMILES

C(O)CC(OCC)OCC

LogP

0.789 (est)

Safety Information

WGK Germany 

3

HS Code 

29094980

MSDS

• Language:English Provider:SigmaAldrich

3,3-DIETHOXY-1-PROPANOL Usage And Synthesis

Uses

3,3-Diethoxy-1-propanol was used in the synthesis of α-acetal-poly(ethylene glycol) via reaction with potassium napthalide and ethylene oxide inside an UniLab Glovebox.

Synthesis

Tetrahydrofuran (THF) was dehydrated through 4Å molecular sieves overnight and set aside. Under nitrogen protection, 2.2 kg of dehydrated THF was added to a 5 L four-necked flask and cooled to below 10 °C. 50 g of lithium aluminum hydride was slowly added, followed by dropwise addition of 250 g of ethyl 3,3-diethoxypropionate, controlling the internal temperature not to exceed 10 °C. After the dropwise addition was completed, the temperature was raised to 20°C and the reaction was carried out for 1 hour. After completion of the reaction, 420 g of distilled water was added and stirred for 2 h. The filtrate was filtered through No. 2 filter paper and the cake was washed with 1.1 kg of THF. The filtrate was concentrated at 40 °C to give 213 g of crude 3,3-diethoxy-1-propanol (abbreviated as 33DEP). 200g of crude 33DEP was taken in a 5L four-necked flask, 1kg of hexane was added and stirred for 1 hour (Step A). Add 1kg of 0.1M phosphate buffer (pH 7.5), stir for 20 minutes and transfer to a 5L separatory funnel and leave to stratify. After separating the aqueous layer, the hexane layer was returned to the flask and the aqueous layer was recovered by repeating the addition of 1 kg of 0.1 M phosphate buffer (pH 7.5), stirring for 20 minutes, and again transferring to a partitioning funnel for stationary partitioning (Step B). The combined aqueous layer was transferred back to a 5L four-necked flask, 2kg of chloroform was added, stirred for 30 minutes, transferred to a 5L partition funnel and left to stratify for 15 minutes. The chloroform layer was recovered and the aqueous layer was repeated once with 2 kg chloroform extraction and the chloroform layers were combined (Step C). The chloroform layer was concentrated at 40°C and residual solvent was removed by nitrogen bubbling. 20g of 4Å molecular sieve was added and filtered after stirring for 5 h to give 188 g of 33DEP. 150 g of 33DEP was taken in a 300 mL four neck flask and subjected to reduced pressure distillation. The first fraction was collected at 0.4 kPa, bath temperature of 38°C, internal temperature of 36°C, and temperature at the top of the tower of 33°C. Subsequently, the bath temperature was gradually increased, and the main fraction was collected at 0.2 kPa, bath temperature of 58 °C, internal temperature of 55 °C, and temperature of the top of the tower of 54 °C, and the temperature of the top of the tower was controlled not to exceed 60 °C, and finally 138 g of the main fraction was obtained (Step D). The main fraction was analyzed by GC and the results are shown in Table 1.

References

[1] Patent: US2012/277477, 2012, A1. Location in patent: Page/Page column 5
[2] Acta Chemica Scandinavica (1947-1973), 1973, vol. 27, p. 239 - 250
[3] Patent: US4634773, 1987, A

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