Allyl bromide → 2-Allyl-4-chloro-6-methoxyphenol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15].C(OCC=C)C=C.C1(C)C=C(C)C=C(C)C=1>>[CH2:15]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([O:9][CH3:10])[C:5]=1[OH:8])[CH:14]=[CH2:13]Participants
Procedure
Treatment of 4-chloro-2-methoxyphenol (30.0 g, 0.19 mol) with sodium hydride (9.1 g, 0.23 mol, 60 wt. %) and allyl bromide (27.46 g, 0.23 mol) followed by treatment of the resultant allyl ether in refluxing mesitylene generally according to the procedure described for Intermediate 8 gave 2-allyl-4-chloro-6-methoxyphenol as a yellow oil. Treatment of 2-allyl-4-chloro-6-methoxyphenol with sodium hydride (7.08 g, 0.177 mol, 60 wt. %) and benzyl bromide (30.27 g, 0.177 mol) generally according to the procedure described for Intermediate 13 provided 1-allyl-2-(benzyloxy)-5-chloro-3-methoxybenzene as a pale yellow oil. Treatment of the olefin (35.5 g, 0.123 mol) of with AD-mix-α (132.0 g) generally according to the procedure described for Intermediate 2 gave 35 g (54%) of (±)-3-[2-(benzyloxy)-5-chloro-3-methoxyphenyl]propane-1,2-diol as a white solid. mp. 65-68° C. Anal. calcd. for C17H19ClO4: C, 63.26; H, 5.93. Found: C, 65.29; H, 6.23.
Sources & evidence
- ORD record
- ord-4d087c70b2864c1d9de6ac69a9cdbf21
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435837B2
Reaction notes
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