4-(4-Chlorophenyl)pent-4-en-1-ol → HCID 20281497, compound

HRID 462889Notes

Reaction equation

HRID 462889 reaction equation
ClC1C=CC(C(=C)CCCO)=CC=1.[CH:14]([CH:16]([CH2:28][CH2:29][CH3:30])[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27])=[CH2:19])=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:15][CH2:14][CH:16]([CH2:28][CH2:29][CH3:30])[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27])=[CH2:19]

Participants

5

Reactant 3

HCID 132358184-(4-Chlorophenyl)pent-4-en-1-olHCID 20281498HCID 20281498, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20281497HCID 20281497, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

By the procedure described for the preparation of 4-(4-chlorophenyl)pent-4-en-1-ol (see Example 1), 4-formyl-2-(2,4-dichlorophenyl)hept-1-ene (1.7 g) and lithium aluminium hydride (0.5 g) in dry diethyl ether (30 ml) gave 4-(hydroxymethyl)-2-(2,4-dichlorophenyl)hept-1-ene (1.55 g, 91%) as a colourless oil, 1H nmr (CDCl3): δ3.52 (2H, d J 6 Hz, CH2OH).

Sources & evidence

ORD record
ord-abd91127b23c45c0ab0b45b2cb0a9bcd
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

Loading…