3-Hydroxybenzyl alcohol → 2-(3-Hydroxymethylphenoxy)phenylacetic acid

HRID 129594

Reaction equation

HRID 129594 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=[O:25].Cl>O.CN(C=O)C>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=[O:25]

Participants

7

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 877542-Bromophenylacetic acid

Product 1

HCID 151257372-(3-Hydroxymethylphenoxy)phenylacetic acidYield 130.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

3-Hydroxybenzyl alcohol (31.0 g) was ground finely and stirred with potassium carbonate (34.6 g), 2-bromophenylacetic acid (26.9 g) and cuprous chloride (large spatula full) under nitrogen. The mixture was warmed to 140° C., and stirred vigorously for 31/2 hours. DMF (60 ml) was then added to the stirred melt and the solution was allowed to cool, poured into water and acidified with dilute hydrochloric acid. The aqueous layer was extracted with ether, and the ether extracts were washed with water, dried and evaporated to give 2-(3-hydroxymethylphenoxy)phenylacetic acid as a brown oil (42.03 g) which was used without further purification.

Workup

  1. temperatureto cool
  2. extractionThe aqueous layer was extracted with ether
  3. washthe ether extracts were washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ccde36f6580d4ba39e2922e675ab5822
Source dataset
uspto-grants-1995_11
Patent number
US05468857

Linked notes

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