4-Hydroxybenzyl Alcohol → Methyl 2-(4-hydroxymethylphenoxy)acetate

HRID 2399499Notes

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]([CH2:23][OH:24])=[CH:21][CH:20]=1.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>>[OH:24][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([O:18][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:20][CH:21]=1

Participants

Reactant 4

HCID 1254-Hydroxybenzyl Alcohol

HCID 996Phenol

HCID 60984Methyl bromoacetate

HCID 86600397Acetone potassium carbonate

Product 1

HCID 690034Methyl 2-(4-hydroxymethylphenoxy)acetateYield 48%

Procedure

Using the K2CO3 /acetone conditions for phenol alkylation described in Step A of Example 30, 8.00 g (64.5. mmol) of 4-hydroxybenzyl alcohol was alkylated with 11.84 g (77.4 mmol) of methyl bromoacetate to afford 6.00 g (48%) of the title compound.

Sources & evidence

ORD record: ord-4f6bdacfbe44486a9fc3061366c841b2
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05449682

Reaction notes

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