Dicyclopentadiene → Cydecanol

HRID 280901Notes

Reaction equation

HRID 280901 reaction equation
[H][H].C([O:8][CH:9]([CH2:17][CH3:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=O)C(C)=C.C(OC(CC)CCCCCCC)(=O)C=C.C1C2C3C=CC(C2C=C1)C3>O>[CH2:13]1[CH:12]2[CH:11]3[CH2:10][CH:9]([OH:8])[CH:17]([CH:16]2[CH:15]=[CH:14]1)[CH2:18]3

Participants

6

Reactant 4

HCID 6492DicyclopentadieneHCID 17853765Deca-8-yl acrylateHCID 22140531Deca-8-yl methacrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 94137Cydecanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound of the formula: ##STR3## wherein Rl is hydrogen or a methyl group, that is, tricyclo-[5.2.1.02,6 ]deca-8-yl methacrylate or tricyclo[5.2.1.02,6 ]-deca-8-yl acrylate, can be prepared by a conventional process for synthesizing a methacrylic or acrylic acid ester. For example, the compound of the formula (I) can be prepared by adding H2O to dicyclopentadiene to give dicyclopentenyl alcohol, which is changed to tricyclo-[5.2.1.02,6 ]deca-8-ol by catalytic hydrogenation reaction, followed by ester exchange reaction with methyl methacrylate or methyl acrylate, or condensation reaction with methacrylic acid, acrylic acid, methacrylic acid chloride or acrylic acid chloride.

Sources & evidence

ORD record
ord-3c3aeb1e64974891ac6318f6cb636213
Source dataset
uspto-grants-1986_05
Patent number
US04591626

Reaction notes

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