Water → Hydroxy(thiophen-2-yl)acetic acid

HRID 27594Notes

Reaction equation

HRID 27594 reaction equation
[OH2:1].[OH-:2].[K+].[Cl-].[Li+].Cl[C:7](Cl)(Cl)[CH:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[OH:9]>O1CCOCC1.C(OCC)C>[S:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[CH:8]([OH:9])[C:7]([OH:2])=[O:1]

Participants

7

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 433294Lithium ChlorideHCID 12566320alpha-Trichloromethyl-2-thiophenemethanol

Product 1

HCID 349855Hydroxy(thiophen-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Into 2.4 ml of water, potassium hydroxide (0.67 g, 12 mmol) and lithium chloride (0.254 g, 6 mmol) were dissolved. Then, into the solution above, α-trichloromethyl-2-thiophenemethanol (0.693 g, 3 mmol) solution in dioxane (2.4 ml) was added and agitation was conducted for 12 hr. at room temperature and for 3 hr. at 80° C. Thereafter, water (20 ml) was added thereto and diethylether was further added into the reaction mixture. The ether soluble part was separated. The water layer was acidified with hydrochloric acid and then, extracted with diethylether. The organic layer was dried with anhydrous magnesium sulfate and was treated with activated carbon and filtered. Thereafter, the filtrate was concentrated and gave 0.246 g of 2-thiopheneglycolic acid as crystals.

Workup

  1. waitat room temperature and for 3 hr
  2. customat 80° C
  3. customThe ether soluble part was separated
  4. extractionextracted with diethylether
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. additionwas treated with activated carbon
  7. filtrationfiltered
  8. concentrationThereafter, the filtrate was concentrated

Sources & evidence

ORD record
ord-c8f460d8f5214d67a7ca573726d7dc2c
Source dataset
uspto-grants-1980_09
Patent number
US04221915

Reaction notes

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