4-Hydroxybenzyl Alcohol → 2-(4-Phenoxymethylphenoxy)-propionic acid

HRID 441415Notes

Reaction equation

HRID 441415 reaction equation
[Na].[C:2]1([OH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC[CH2:11][C:12]1[CH:23]=[CH:22][C:15]([O:16][CH:17]([CH3:21])[C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1.C1C(CO)=CC=C(O)C=1.BrC(C)C(OCC)=O.OCC1C=CC(OC(C)C(O)=O)=CC=1>C(O)C>[O:8]([CH2:11][C:12]1[CH:23]=[CH:22][C:15]([O:16][CH:17]([CH3:21])[C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 1254-Hydroxybenzyl AlcoholHCID 996PhenolHCID 79040Ethyl 2-bromopropionateHCID 3519242-[4-(Hydroxymethyl)phenoxy]propanoic acidHCID 5360545SodiumHCID 571899592-(p-Bromoethylphenoxy)-propionic acid

Product 1

HCID 214211732-(4-Phenoxymethylphenoxy)-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.3 g. of sodium is dissolved in 250 ml. of absolute ethanol; 9.4 g. of phenol and 28.6 g. of the ethyl ester of 2-(p-bromoethylphenoxy)-propionic acid [obtainable by reacting p-hydroxybenzyl alcohol with ethyl 2-bromopropionate to the ethyl ester of 2-(p-hydroxymethylphenoxy)-propionic acid and subsequent reaction with SOBr2 ] are added thereto, and the mixture is refluxed for 3 hours and evaporated. The usual working-up procedure yields the ethyl ester of 2-(4-phenoxymethylphenoxy)-propionic acid. Analogously, the ethyl ester of 2-(4-phenoxymethylphenoxy)-2-methylpropionic acid is obtained from the ethyl ester of 2-p-bromomethylphenoxyisobutyric acid (obtainable by bromination of the ethyl ester of 2-p-methylphenoxyisobutyric acid with N-bromosuccinimide);

Workup

  1. additionare added
  2. temperaturethe mixture is refluxed for 3 hours
  3. customevaporated

Sources & evidence

ORD record
ord-61e8a8cd51c44809b1f1726acb960e76
Source dataset
uspto-grants-1977_08
Patent number
US04039683

Reaction notes

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