Hydrochloric Acid → 3-(Hydroxymethyl)-2-thiophenecarboxylic acid

HRID 1011416Notes

Reaction equation

HRID 1011416 reaction equation
C(N[C:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH:11]([OH:13])C)=[O:5])C.Cl.[OH-].[Na+].C(=O)(O)[O-:18].[Na+]>>[OH:13][CH2:11][C:10]1[CH:9]=[CH:8][S:7][C:6]=1[C:4]([OH:5])=[O:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5323822HCID 5323822, compound

Product 1

HCID 200942743-(Hydroxymethyl)-2-thiophenecarboxylic acidYield 10%

Procedure

A solution of 3-(1-Hydroxy-ethyl)-thiophene-2-carboxylic acid ethylamide (298 mg, 1.5 mmol) in 15 ml of aqueous 6N HCl solution is heated at 100° C. for 1.5 h. The reaction mixture is cooled to room temperature and the pH is adjusted to ˜8.5 with 30% aqueous NaOH solution and saturated aqueous sodium bicarbonate solution. The resulting solution is extracted with Dichloromethane. The aqueous layer is collected and acidified with aqueous 6N HCl until the pH˜1. The resulting solution is extracted with tBuOH-Ether. The combined organic extracts are dried and concentrated to give the title compound (25 mg, 10%).

Workup

  1. extractionThe resulting solution is extracted with Dichloromethane
  2. customThe aqueous layer is collected
  3. extractionThe resulting solution is extracted with tBuOH-Ether
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a41bdfe756c491b9325654c062c70b1
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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