4-Methylmorpholine → 1,4-Cyclohexanedimethanol

HRID 478122

Reaction equation

HRID 478122 reaction equation
[C@H:1]1([CH2:9][OH:10])[CH2:6][CH2:5][C@H:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.CN1CCOCC1.P(Cl)(Cl)(=O)OCCCCCC>C(Cl)Cl>[CH2:3]1[CH:4]([CH2:7][OH:8])[CH2:5][CH2:6][CH:1]([CH2:9][OH:10])[CH2:2]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 6422909Phosphorodichloridic acid, hexyl esterHCID 178520956HCID 178520956, compound

Product 1

HCID 77351,4-Cyclohexanedimethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-40 °C

Procedure

Under an argon stream, 10 g of trans-1,4-cyclohexane dimethanol (CHDM), 15.25 mL (14.03 g) of N-methyl morpholine (NMM), and 50 mL of methylene chloride were transferred into a 250 mL flash equipped with a funnel. The solution in the flask was cooled down to −40° C. with stirring. A solution of 15.19 g of hexyl phosphoro-dichloridate (HOP) in 20 mL of methylene chloride was added through the funnel, and an additional 10 mL of methylene chloride was used to flush through the funnel. The mixture was then brought up to room temperature gradually and kept stirring for four hours.

Workup

  1. customequipped with a funnel
  2. customto flush through the funnel
  3. customwas then brought up to room temperature
  4. stirringkept stirring for four hours

Sources & evidence

ORD record
ord-f2994ca8f3984b3c9380f9c80433af2f
Source dataset
uspto-grants-2003_11
Patent number
US06641833B2

Linked notes

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