Hydrochloric Acid → HCID 10709041, compound

HRID 1977924Notes

Reaction equation

HRID 1977924 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[C:8]([C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])=[O:9])[CH:2]=[CH2:3].Cl.[CH3:23]O>>[CH3:23][O:13][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=1[C:8](=[O:9])[C:7]1[CH:19]=[CH:20][CH:21]=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10708017HCID 10708017, compound

Product 1

HCID 10709041HCID 10709041, compoundYield 100%

Procedure

A solution of 2-[3-(allyloxy)benzoyl]benzoic acid (9.00 g, 31.9 mmol) in methanol (100 mL) was saturated with hydrogen chloride gas. The resulting solution was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and diluted with diethyl ether. The resulting solution was washed sequentially with a saturated sodium bicarbonate solution, water, and a saturated sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting pale yellow oil solidified upon standing to provide 9.45 g (100%) of the desired title product as a white solid: mp 50-52° C.; NMR (CDCl3) 8.05 (d, J=7.8 Hz, 1H), 7.65 (t, J=8 Hz, 1H), 7.56 (t, J=8 Hz, 1H), 7.40 (m, 2H), 7.32 (t, J=8 Hz, 1H), 7.22 (d, J=8 Hz, 1H), 7.14 (d, J=8 Hz, 1H), 6.08 (m, 1H), 5.40 (d, J=16 Hz, 1H), 5.30 (d, J=11 Hz, 1H), 4.78 (d, J=4 Hz, 2H), 3.62 (s, 3H); MS-FD m/e 297 (p+1, 40), 296 (p, 100); IR.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with diethyl ether
  3. washThe resulting solution was washed sequentially with a saturated sodium bicarbonate solution, water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63bfa33402f44a8f96dec7cee76ffd7f
Source dataset
uspto-grants-2001_05
Patent number
US06235785B1

Reaction notes

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