Phenol → Methyl 2-(2,6-dichloro-4-hydroxymethylphenoxy)-2-phenylacetate

HRID 1492582Notes

Reaction equation

HRID 1492582 reaction equation
C([O-])([O-])=O.[K+].[K+].CC(C)=O.C1(O)C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:28])[C:26]=1[OH:27])[CH2:22][OH:23].Br[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][C:37]([O:39][CH3:40])=[O:38]>>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:22][OH:23])[CH:24]=[C:25]([Cl:28])[C:26]=1[O:27][CH:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:30]=1)[C:37]([O:39][CH3:40])=[O:38]

Participants

5

Reactant 4

HCID 996PhenolHCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-HCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 86600397Acetone potassium carbonate

Product 1

HCID 19385731Methyl 2-(2,6-dichloro-4-hydroxymethylphenoxy)-2-phenylacetateYield 20.4%

Procedure

Using the K2CO3 /acetone conditions for phenol alkylation described in Step A of Example 4, 0.400 g (2.07 mmol) of the product of Step C was alkylated with 0.522 g (2.28 mmol) of methyl 2-bromophenylacetate to afford 0.144 g (20%) of the title compound.

Sources & evidence

ORD record
ord-2b06a122c14e43fa81a1e8a1b312bcd5
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

Loading…