Glyoxylic Acid → 2-(3,4-Dihydro-6-methoxy-1-oxo-2(1H)-naphthalenylidene)acetic acid

HRID 1506780Notes

Reaction equation

HRID 1506780 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]2.S(=O)(=O)(O)O>COCCOCCOC>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[C:14](=[CH:2][C:1]([OH:5])=[O:4])[CH2:13][CH2:12]2

Participants

6

Reactant 4

HCID 760Glyoxylic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 730967892-(3,4-Dihydro-6-methoxy-1-oxo-2(1H)-naphthalenylidene)acetic acidYield 88.5%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
110 °C

Procedure

Glyoxalic acid (190 mL, 1702 mmol) and water (180 mL) were added to a stirred solution of 6-methoxy tetralone (300 g, 1702 mmol) in diglyme (600 mL) followed by sulfuric acid (80 mL, 1500 mmol). The reaction mixture was heated to 110° C. overnight. The reaction mixture was cooled to 0° C., and resulting solids were filtered off and washed with water (3×200 mL), dried under reduced pressure to afford the title compound (350 g, 88%) as a solid. 1H NMR (300 MHz, DMSO-d6): δ 12.9 (bs, 1H), 7.9 (d, J=8.4 Hz, 1H), 7.0 (m, 2H), 6.6 (s, 1H), 3.8 (s, 3H), 3.3 (m, 2H), 3.0 (m, 2H). ESI-MS m/z: 233 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customresulting solids
  3. filtrationwere filtered off
  4. washwashed with water (3×200 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-08e4ba3c90a44bf5ba14d60f7b2378fc
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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