Benzyl Bromide → HCID 68583816, compound

HRID 13917Notes

Reaction equation

HRID 13917 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]=1[OH:14])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:21]([O:14][C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=[CH:13][C:4]=1[CH2:1][CH:2]=[CH2:3])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 685832872-(Prop-2-en-1-yl)-5,6,7,8-tetrahydronaphthalen-1-ol

Product 1

HCID 68583816HCID 68583816, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

Treatment of 2-allyl-5,6,7,8-tetrahydronaphthalen-1-ol (18.48 g, 0.098 mol) with potassium carbonate (41.46 g, 0.300 mol), benzyl bromide (18.81 g, 0.110 mol), and tetrabutylammonium iodide (7.39 g, 0.020 mol) generally according to the procedure described for Intermediate 1 afforded 24.05 g (88%) of 2-allyl-5,6,7,8-tetrahydronaphthalen-1-yl benzyl ether as a pale yellow oil. Rf=0.39 (silica, ethyl acetate:hexanes 1:19); Anal. calcd. for C20H22O0.2H2O: C, 85.19; H, 8.01. Found: C, 84.95; H, 7.75.

Sources & evidence

ORD record
ord-4af40855a52e4385bf6d7111eeefc971
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

Loading…