Acetic Acid → 2-(2,3-Dihydrobenzofuran-5-yl)-2-hydroxyacetic acid

HRID 904020Notes

Reaction equation

HRID 904020 reaction equation
N[CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)[C:3]([OH:5])=[O:4].C(O)(=[O:17])C.N([O-])=O.[Na+]>O>[OH:17][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 205312232-Amino-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acidHCID 23668193Sodium Nitrite

Product 1

HCID 233358212-(2,3-Dihydrobenzofuran-5-yl)-2-hydroxyacetic acidYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

α-Amino(2,3-dihydro-5-benzofuranyl)acetic acid (200 mg, 1.04 mmole) is dissolved in 250 mg (4.14 mmole) of glacial acetic acid and 145 mg (2.08 mmole) of sodium nitrite in about 5 ml of water is added dropwise. An additional 1 ml of glacial acetic acid is added and the mixture is heated to 65° C. and held at 65° C. for 4 hours. After cooling the reaction mixture is diluted with water and extracted with ethyl acetate for several hours. The ethyl acetate is dried over magnesium sulfate, filtered and evaporated to give a 65% yield of the title compound. NMR(DMSO-D6)ppm(δ)7.15(m,3); 5.18(d,1); 4.78(t,2) and 3.34(t,2).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with ethyl acetate for several hours
  3. dry with materialThe ethyl acetate is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-91943073a95d4debbc8dabfad8ed52b3
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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