Methanol → 4-(2-Hydroxyethoxy)benzenecarboxylic acid

HRID 2198686Notes

Reaction equation

HRID 2198686 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.CO.O.C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O.CCOCC>[OH:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 128104744-(2-Tetrahydropyranyloxyethoxy)benzoic acid

Product 1

HCID 43122544-(2-Hydroxyethoxy)benzenecarboxylic acid

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 7.7 g (37.7 mmol) of 4-(2-tetrahydropyranyloxyethoxy)benzoic acid and 31 ml (754 mmol) of anhydrous methanol, at RT, is added 2 drops of conc. sulfuric acid. The mixture is stirred at RT for 1 day and is then rotoevaporated to near dryness. To the residue is added 100 ml water, 50 ml ether and 30 ml aqueous 15% potassium carbonate, and the mixture is stirred until the solid is dissolved. The organic phase is separated and discarded; 150 ml of ethyl acetate and 50 ml of aqueous 3 N sulfuric acid are added to the remaining aqueous phase. The aqueous phase is then separated and extracted with ethyl acetate (80 ml, 3X). The combined organic phases are washed with aqueous saturated sodium chloride (50 ml, 2X) and then dried over calcium sulfate. Removal of solvent by rotoevaporation gives 4-(hydroxyethoxy)benzoic acid.

Workup

  1. stirringthe mixture is stirred until the solid
  2. dissolutionis dissolved
  3. customThe organic phase is separated
  4. addition150 ml of ethyl acetate and 50 ml of aqueous 3 N sulfuric acid are added to the remaining aqueous phase
  5. customThe aqueous phase is then separated
  6. extractionextracted with ethyl acetate (80 ml, 3X)
  7. washThe combined organic phases are washed with aqueous saturated sodium chloride (50 ml, 2X)
  8. dry with materialdried over calcium sulfate
  9. customRemoval of solvent by rotoevaporation

Sources & evidence

ORD record
ord-531c82f3c1404cb48589a8b5f383c9fa
Source dataset
uspto-grants-1982_11
Patent number
US04359424

Reaction notes

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