Hydrochloric Acid → HCID 66886391, compound

HRID 75194Notes

Reaction equation

HRID 75194 reaction equation
C([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]#[N:13])[CH2:7][CH2:6]1)=C.Cl.O>ClCCl.O1CCOCC1>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]#[N:13])[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 66887075HCID 66887075, compound

Product 1

HCID 66886391HCID 66886391, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

4-[(Vinyloxy)methyl]cyclohexylacetonitrile (0.9 g, 0.005 mol) was dissolved in dichloromethane (5 mL), and 1.5 mL of 4 N hydrogen chloride (0.22 g, 0.0060 mol) in dioxane was added with water (0.2 mL). The reaction was stirred for 30 min. and then concentrated to give the product as a 3:1 mixture of diastereomers, (0.75 g). 1H NMR (400 MHz, CDCl3): δ 3.451-3.467 d, 2H, J=6.4 Hz), 2.58 (br s, 1H), 2.271-2.288 (d, 2H, J=6.8 Hz), 1.85-1.93 (m, 4H), 1.2-1.8 (m, 4H), 0.95-1.19 (m, 4H) (major diastereomer).

Workup

  1. concentrationconcentrated
  2. customto give the product
  3. additionas a 3:1 mixture of diastereomers, (0.75 g)

Sources & evidence

ORD record
ord-abe982b83498492883f07b44903ce554
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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