Water → HCID 21896325, compound

HRID 719066Notes

Reaction equation

HRID 719066 reaction equation
[CH:1]12[O:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:8]([OH:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21].O>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:19]([O:11][C:8]([CH:2]1[CH2:3][CH:4]2[O:7][CH:1]1[CH2:6][CH2:5]2)([CH3:9])[CH3:10])(=[O:22])[CH:20]=[CH2:21]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 2651162-(7-oxabicyclo[2.2.1]hept-2-yl)propan-2-ol

Product 1

HCID 21896325HCID 21896325, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

In 80 ml of toluene were dissolved 12.5 g of 2-(7-oxanorbornan-2-yl)-2-propanol, 12.1 g of triethylamine, and 0.4 g of 4-(N,N-dimethylamino)pyridine. Then 9.1 g of acrylic chloride was added to the solution at 50° C., which was stirred at the temperature for one hour. Water, 50 ml, was added to the solution below 30° C., followed by ordinary post-treatment. Vacuum distillation yielded 13.8 g of 2-(7-oxanorbornan-2-yl)-2-propyl acrylate. The two-step yield was 82%.

Workup

  1. distillationVacuum distillation

Sources & evidence

ORD record
ord-24d8307f6c7145ee84ee5837f631b7ff
Source dataset
uspto-grants-2006_11
Patent number
US07132215B2

Reaction notes

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