Benzyl Bromide → HCID 68961793, compound

HRID 2115912Notes

Reaction equation

HRID 2115912 reaction equation
C(C1C=CC=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]=1[OH:17])C=C.C(=O)([O-])[O-:19].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(C1C=CC=C(CC2C=CC=CC=2)C=1[O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)C=C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(C)(C)C>[CH2:24]([C:15]1[C:16]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[C:11]([CH2:10][CH:6]([OH:19])[CH2:5][OH:17])[CH:12]=[CH:13][CH:14]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68963743HCID 68963743, compoundHCID 68964298HCID 68964298, compound2×

Product 1

HCID 68961793HCID 68961793, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6386tert-ButanolSolvent

Procedure

Treatment of 2-allyl-6-benzylphenol (12.11 g, 0.054 mol) with potassium carbonate (30.00 g, 0.217 mol), benzyl bromide (10.67 g, 0.062 mol), and tetrabutylammonium iodide (2.01 g, 0.005 mol) generally according to the procedure described for Intermediate 1 provided 1-allyl-3-benzyl-2-(benzyloxy)benzene. Treatment of 1-allyl-3-benzyl-2-(benzyloxy)benzene (16.35 g, 0.052 mol) with AD-mix-ox (76.02 g) generally according to the procedure described for Intermediate 2 gave 9.82 (54%, 25% ee) of (±)-3-[3-benzyl-2-(benzyloxy)phenyl]propane-1,2-diol as a white crystalline solid. mp 55-58° C.; Anal. calcd. for C23H24O3: C, 79.28; H, 6.94. Found: C, 78.89; H, 6.96.

Sources & evidence

ORD record
ord-926e892ded194a5692b05022599f1bf9
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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