Formaldehyde → 1,3-Propanediol, 2-methyl-2-(1-methylpropyl)-

HRID 573459

Reaction equation

HRID 573459 reaction equation
[OH-:1].[Na+].[CH3:3][CH:4]([CH:7]([CH3:10])[CH2:8][CH3:9])[CH:5]=[O:6].[CH2:11]=O>>[CH:7]([C:4]([CH3:11])([CH2:3][OH:1])[CH2:5][OH:6])([CH2:8][CH3:9])[CH3:10]

Participants

4

Conditions

Temperature
40 °C

Procedure

An aqueous NaOH solution (30%, 420 g) was added at room temperature into a stirred mixture of 2,3-dimethyl pentanal (325 g, prepared as above in EXAMPLE II) and aqueous formaldehyde solution (CH2O) (30%, 722 g) while the reaction temperature was allowed to rise up to about 80° C. due to the exothermic reaction. After the addition was completed, the reaction mixture was cooled to about 40° C. The organic phases was separated and fractionally distilled to afford 2-sec-butyl-2-methyl-propane-1,3-diol (277 g). 2-sec-Butyl-2-methyl-propane-1,3-diol was reacted with 2,4-dimethyl-cyclohex-3-enecarbaldehyde to afford 5-sec-butyl-2-(2,4-dimethyl-cyclohex-3-enyl)-5-methyl-[1,3]dioxane according to previous disclosure (See, for example, U.S. Pat. No. 6,444,637).

Workup

  1. customto rise up to about 80° C. due to the exothermic reaction
  2. additionAfter the addition
  3. customThe organic phases was separated
  4. distillationfractionally distilled

Sources & evidence

ORD record
ord-e15402fe95b447028ec57da5cff0d90b
Source dataset
uspto-grants-2015_05
Patent number
US09029576B2

Linked notes

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