Water → HCID 21896333, compound

HRID 719068Notes

Reaction equation

HRID 719068 reaction equation
[CH:1]12[O:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:8]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23].O>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:21]([O:13][C:8]1([CH:2]2[CH2:3][CH:4]3[O:7][CH:1]2[CH2:6][CH2:5]3)[CH2:9][CH2:10][CH2:11][CH2:12]1)(=[O:24])[CH:22]=[CH2:23]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 21896328HCID 21896328, compound

Product 1

HCID 21896333HCID 21896333, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

In 80 ml of toluene were dissolved 18.2 g of 1-(7-oxanorbornan-2-yl)cyclopentanol, 15.2 g of triethylamine, and 0.5 g of 4-(N,N-dimethylamino)pyridine. Then 12.5 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 19.7 g of 1-(7-oxanorbornan-2-yl)cyclopentyl acrylate. The two-step yield was 84%.

Workup

  1. distillationVacuum distillation

Sources & evidence

ORD record
ord-7cb28ccf8ed24aec9fb589f37221e7a7
Source dataset
uspto-grants-2006_11
Patent number
US07132215B2

Reaction notes

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