3-Phenoxybenzyl alcohol → HCID 54463321, compound

HRID 485719Notes

Reaction equation

HRID 485719 reaction equation
[CH3:1][C:2]1([CH3:12])[C@H:4]([CH:5]=[C:6]=[CH:7][Br:8])[C@H:3]1[C:9]([OH:11])=[O:10].[O:13]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:1][C:2]1([CH3:12])[C@H:4]([CH:5]=[C:6]=[CH:7][Br:8])[C@H:3]1[C:9]([O:11][CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:21]=1)=[O:10]

Participants

3

Reactant 2

HCID 262953-Phenoxybenzyl alcoholHCID 131714317HCID 131714317, compound

Product 1

HCID 54463321HCID 54463321, compound

Procedure

Using the procudure of Example 1, 1.2 g of the acid of Example 29 and 1 g of 3-phenoxy-benzyl alcohol were reacted to obtain after chromatography over silica gel and elution with a 9-1 hexane-ethyl acetate mixture 1.49 g of 3-phenoxybenzyl (1R,trans) 2,2-dimethyl-3-(3-bromo-1,2-propadienyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+15.5°±2° (c=0.5% in chloroform).

Workup

  1. customwere reacted
  2. customto obtain after chromatography
  3. washover silica gel and elution with a 9-1 hexane-ethyl acetate mixture 1.49 g of 3-phenoxybenzyl (1R,trans) 2,2-dimethyl-3-(3-bromo-1,2-propadienyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+15.5°±2° (c=0.5% in chloroform)

Sources & evidence

ORD record
ord-86843426f0274785bab7e24acd6241d3
Source dataset
uspto-grants-1985_08
Patent number
US04537897

Reaction notes

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