Ethyl 3-phenylprop-2-enoate → 3-Phenylprop-2-En-1-Ol

HRID 1590380Notes

Reaction equation

HRID 1590380 reaction equation
[C:1](OCC)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>CCCCCC.ClCCl>[C:4]1([CH:3]=[CH:2][CH2:1][OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 7649Ethyl 3-phenylprop-2-enoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 3083-Phenylprop-2-En-1-OlYield 104.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

The above ester (3.52 g) was treated with diisobutylaluminium hydride (40 ml of a 1M solution in hexane) in dichloromethane (40 ml) in the normal fashion to provide 3-phenylprop-2-en-1-ol (2.8 g). NMR 1H: 7.2(5H,m), 6.55(1H,d), 6.35 (1H,t), 4.25(2H,d), 1.97(1H,s).

Sources & evidence

ORD record
ord-9d68c49d44e541e5a5c4884fa6c373b2
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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