Acetic Acid → 1,3-Bis(1-methylethoxy)-2-propanol

HRID 1050889

Reaction equation

HRID 1050889 reaction equation
[CH:1]([O:4][CH2:5][CH:6]1[CH2:8][O:7]1)([CH3:3])[CH3:2].[CH3:9][CH:10]([CH3:12])[O-:11].[K+].C(O)(=O)C>CCCCCC.C(O)(C)C>[CH:10]([O:11][CH2:8][CH:6]([OH:7])[CH2:5][O:4][CH:1]([CH3:3])[CH3:2])([CH3:12])[CH3:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 199202-((1-Methylethoxy)methyl)oxiraneHCID 23663646Potassium propan-2-olate

Product 1

HCID 830521,3-Bis(1-methylethoxy)-2-propanol

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

2-(Isopropoxymethyl)oxirane (23.23 g, 25.1 mL, 200 mmol) was dissolved in hexane (20 mL) and placed in reactor. Separately (1.2 g, 20 mmol) of KH was slowly added to (90.1 g, 115 mL, 1.5 Mol) of isopropanol at RT. After deprotonation was complete the solution of potassium isopropoxide in isopropanol was added to the reactor. All operations were performed in a glove box. The reactor was sealed and heated 80° C. for 24 hours. After cooling acetic acid (20 mmols) and ca. 5 g. of powdered talc were added to the reaction mixture followed by filtration through a plug of celite. The solvent was evaporated and the residue distilled under vacuum affording 20.09 g of 1,3-diisopropoxypropan-2-ol.

Workup

  1. customplaced in reactor
  2. additionwas added to the reactor
  3. customAll operations were performed in a glove box
  4. customThe reactor was sealed
  5. filtrationfollowed by filtration through a plug of celite
  6. customThe solvent was evaporated
  7. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-058682eadab8481ea18e4183af0407f7
Source dataset
uspto-grants-2016_07
Patent number
US09388106B2

Linked notes

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