Glyoxylic Acid → 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid

HRID 1187024Notes

Reaction equation

HRID 1187024 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[C:11]([OH:15])(=[O:14])[CH:12]=O>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][O:10][CH:12]2[C:11]([OH:15])=[O:14]

Participants

3

Reactant 2

HCID 760Glyoxylic AcidHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 666464675-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid

Procedure

A solution of 2-(2-bromophenyl)ethanol (40 g, 0.2 mol) and glyoxylic acid (16 g, 0.22 mol) in 100 mL of trifluoacetic acid was refluxed overnight. The solvent was concentrated. Water and ammonium hydroxide was added to the residue to adjust the pH of the solution over 7. The solution was extracted with diethyl ether, and the aqueous layer was adjusted to about 3 with 1M HCl, and then the solution was extracted with ethyl acetate. The organic layer was dried and evaporated. The residue was without purification to give 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid. 1H-NMR (400 MHz, CDCl3) δ 7.52 (d, J=7.6 Hz, 1H), 7.12 (t, J=7.8 Hz, 2H), 5.33 (s, 1H), 4.27˜4.33 (m, 1H), 3.99˜4.06 (m, 1H), 2.87˜2.89 (m, 2H).

Workup

  1. concentrationThe solvent was concentrated
  2. additionWater and ammonium hydroxide was added to the residue
  3. extractionThe solution was extracted with diethyl ether
  4. extractionthe solution was extracted with ethyl acetate
  5. customThe organic layer was dried
  6. customevaporated
  7. customThe residue was without purification

Sources & evidence

ORD record
ord-f7fbd8d3cc6e404384372b17cfd019d3
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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