Phenol → Methyl 2-(4-formyl-2-methylphenoxy)phenylacetate

HRID 2399484Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].CC(C)=O.C1(O)C=CC=CC=1.[OH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=1[CH3:27].Br[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][C:36]([O:38][CH3:39])=[O:37]>>[CH:23]([C:22]1[CH:25]=[CH:26][C:19]([O:18][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:20]([CH3:27])[CH:21]=1)=[O:24]

Participants

Reactant 4

HCID 996Phenol

HCID 1399014-Hydroxy-3-methylbenzaldehyde

HCID 8063364Methyl 2-(2-bromophenyl)acetate

HCID 86600397Acetone potassium carbonate

Product 1

HCID 19385660Methyl 2-(4-formyl-2-methylphenoxy)phenylacetateYield 96%

Procedure

Using the K2CO3 /acetone conditions for phenol alkylation described in Step A of Example 30, 0.50 g (3.68 mmol) of 4-hydroxy-3-methylbenzaldehyde was alkylated with 0.926 g (4.05 mmol) of methyl 2-bromophenylacetate to afford 1.00 g (96%) of the title compound.

Sources & evidence

ORD record: ord-f52b57eac02446f0be03cbd9cf19fbcc
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05449682

Reaction notes

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