Methanol → 3-(4-Phenylphenoxy)-2-hydroxypropylazide

HRID 1901732Notes

Reaction equation

HRID 1901732 reaction equation
[C:1]1([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][CH:13]3[CH2:15][O:14]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:18]=[N+:19]=[N-:20].[Na+].C(OC)=O.CO>O>[C:1]1([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][CH:13]([OH:14])[CH2:15][N:18]=[N+:19]=[N-:20])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 1073251-(Biphenyl-4-yloxy)-2,3-epoxypropane

Product 1

HCID 214747683-(4-Phenylphenoxy)-2-hydroxypropylazideYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 3.00 g of 4-phenylphenoxymethyloxirane (prepared as described in Preparation 82), 4.23 g of sodium azide, 15 ml of methyl formate and 90 ml of an 8:1 by volume mixture of methanol and water were used, to give 3.09 g of the title compound, melting at 72.2° to 73.9° C.

Workup

  1. customA procedure similar to that described in Preparation 12

Sources & evidence

ORD record
ord-c114dbcc2fa14910b52635be5c3746e7
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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