Guaiacol → HCID 10967048, compound

HRID 2115935Notes

Reaction equation

HRID 2115935 reaction equation
C1(OC)C(=CC=CC=1)O.C(Br)C=C.C(=O)([O-])[O-].[K+].[K+].C(OCC=C)C=C.[CH2:27]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[C:31]=1[OH:38])[CH:28]=[CH2:29].C1(O)C=CC=CC=1.[CH2:46](Br)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C1(C)C=C(C)C=C(C)C=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(C)(C)C>[CH2:27]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[C:31]=1[O:38][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH:28]=[CH2:29]

Participants

11

Reactant 7

HCID 460GuaiacolHCID 996PhenolHCID 7498Benzyl BromideHCID 7841Allyl bromideHCID 11194Diallyl etherHCID 11430Potassium Carbonate2×HCID 3475772-Methoxy-6-(prop-2-en-1-yl)phenol

Product 1

HCID 10967048HCID 10967048, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6386tert-ButanolSolventHCID 7947MesityleneSolvent

Procedure

Treatment of guaiacol (25.00 g, 0.201 mol) with allyl bromide (29.24 g, 0.242 mol) and potassium carbonate (83.50 g, 0.604 mol) followed by refluxing the resultant allyl ether in mesitylene generally according to the procedure described for Intermediate 8 afforded 2-allyl-6-methoxyphenol as a brown oil. Treatment of the phenol with potassium carbonate (83.5 g, 0.604 mol), benzyl bromide (36.19 g, 0.212 mol), and tetrabutylammonium iodide (7.42 g, 0.020 mol) generally according to the procedure described for Intermediate 1 gave 23.61 g (45%) of 1-allyl-2-(benzyloxy)-3-methoxybenzene as a pale yellow oil. Rf=0.71 (silica, ethyl acetate:hexanes 1:9); Anal. calcd. for C17H18O2: C, 80.28; H, 7.13. Found: C, 79.09; H, 6.93.

Sources & evidence

ORD record
ord-2635616f4f0c46fb922d7ccf270fe0c7
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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