1,3-Dioxane-5-carboxaldehyde, 2,2,5-trimethyl- (9CI)

Base Information

• Chemical Name: 1,3-Dioxane-5-carboxaldehyde, 2,2,5-trimethyl- (9CI)
• CAS No.: 138517-53-0
• Molecular Formula: C8H14O3
• Molecular Weight: 158.19496
• Mol file: 138517-53-0.mol

Synonyms:1,3-Dioxane-5-carboxaldehyde, 2,2,5-trimethyl- (9CI)

Chemical Property of 1,3-Dioxane-5-carboxaldehyde, 2,2,5-trimethyl- (9CI)

Chemical Property:

• Boiling Point: 200.3±25.0 °C(Predicted)
• PSA: 35.53000
• Density: 1.041±0.06 g/cm3(Predicted)
• LogP: 0.97450

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3-Dioxane-5-carboxaldehyde, 2,2,5-trimethyl- (9CI)

There total 1 articles about 1,3-Dioxane-5-carboxaldehyde, 2,2,5-trimethyl- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane (3663-46-5) → 5-(2,2,5-trimethyl-1,3-dioxane)carbaldehyde (138517-53-0)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; In dichloromethane; water; at 20 ℃; for 0.583333h; Inert atmosphere;

DOI:10.1021/ja411270d

Reference yield:

5-(2,2,5-trimethyl-1,3-dioxane)carbaldehyde (138517-53-0) → (2R,4S,5S,6R)-4-hydroxy-6-(2-hydroxyethyl)-5-hydroxymethyl-5-methyltetrahydropyran-2-ylmethyl benzoate (635727-04-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

1.2: aq. NaOH / 0 °C

2.1: trifluoroacetic acid / toluene / -20 - 0 °C

3.1: (COCl)2; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

4.2: aq. NaOH / 0 °C

5.1: iodine; K₂CO₃ / acetonitrile / -30 - -20 °C

6.1: 1-methyl-pyrrolidin-2-one / 100 °C

7.1: O₃; NaHCO₃ / methanol / -78 °C

7.2: NaBH₄ / methanol / 0 °C

8.1: H₂; HOAc / Pd/C / methanol / 20 °C

With oxalyl dichloride; 4 A molecular sieve; hydrogen; iodine; sodium hydrogencarbonate; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; acetonitrile; 3.1: Swern oxidation;

DOI:10.1002/anie.200352016

Reference yield:

5-(2,2,5-trimethyl-1,3-dioxane)carbaldehyde (138517-53-0) → benzoic acid 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (635727-24-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

1.2: aq. NaOH / 0 °C

2.1: trifluoroacetic acid / toluene / -20 - 0 °C

3.1: (COCl)2; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

4.2: aq. NaOH / 0 °C

5.1: iodine; K₂CO₃ / acetonitrile / -30 - -20 °C

6.1: 1-methyl-pyrrolidin-2-one / 100 °C

7.1: O₃; NaHCO₃ / methanol / -78 °C

7.2: NaBH₄ / methanol / 0 °C

8.1: H₂; HOAc / Pd/C / methanol / 20 °C

9.1: imidazole / dimethylformamide / 0 °C

With 1H-imidazole; oxalyl dichloride; 4 A molecular sieve; hydrogen; iodine; sodium hydrogencarbonate; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Swern oxidation;

DOI:10.1002/anie.200352016

upstream raw materials:

5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

Downstream raw materials:

{(2R,4S,5S)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl}methanol

(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

(2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane

(2R,4S,5S,6R)-4-hydroxy-6-(2-hydroxyethyl)-5-hydroxymethyl-5-methyltetrahydropyran-2-ylmethyl benzoate

Refernces

• 1、 Trost, Barry M.,Stivala, Craig E.,Hull, Kami L.,Huang, Audris,Fandrick, Daniel R.. "A concise synthesis of (-)-lasonolide A". supporting information. p. 88 - 91. Retrieved 2014/01/23.
• 2、 Archambeau, Alexis,Miege, Frederic,Meyer, Christophe,Cossy, Janine. "Highly efficient stereoselective catalytic C(sp3)-H insertions with donor rhodium carbenoids generated from cyclopropenes". supporting information. p. 11540 - 11544. Retrieved 2013/01/15.