Hydrochloric Acid → HCID 53634723, compound

HRID 1590385Notes

Reaction equation

HRID 1590385 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:7])C.[H-].C([Al+]CC(C)C)C(C)C.Cl>ClCCl.CCCCCC>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]([CH3:7])=[CH:5][CH2:4][OH:3])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 360612HCID 360612, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 53634723HCID 53634723, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

The above ester (1.44 g) was dissolved in dichloromethane (13 ml) and cooled to -20°. Diisobutylaluminium hydride (12.8 ml of a 1M solution in hexane) was added dropwise. After 18 hours at 25° dilute hydrochloric acid was added carefully and the mixture worked up in the usual manner to give 3-(4-chlorophenyl)but-2-en-1-ol (0.44 g). NMR 1H: 7.18(4H,s), 5.85(1H,t), 4.25(2H,d), 3.05(1H,s), 2.05(3H,s).

Workup

  1. temperaturecooled to -20°

Sources & evidence

ORD record
ord-0adc0414f7d94ba2aa1e542016bff885
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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