Hydrochloric Acid → HCID 68793838, compound

HRID 2217620Notes

Reaction equation

HRID 2217620 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)(=O)C.[OH-].[Li+].Cl>C1COCC1.O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[CH:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 687943372-(4-Acetoxyphenyl)-3-p-tolylacrylic acid

Product 1

HCID 68793838HCID 68793838, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 37 (20.16 g, 68.1 mmol) in 100 mL THF was added a solution of lithium hydroxide (5.7 g, 237.5 mmol) in 100 mL water. The reaction was allowed to stir at room temperature for 16 h after which 5% HCl in water was added to pH=1. The yellow solid was filtered and recrystallized out of toluene, washed with hexane and dried under vacuum to yield a white solid (14.27 g, 82.5%). 1H NMR (400 MHz, DMSO-d6) δ 12.46 (br s, 1H), 9.47 (br s, 1H), 7.63 (s, 1H), 7.02 (d, J=8.0 Hz, 2H), 6.97 (d, J=8.4 Hz, 2H), 6.93 (d, J=8.4 Hz, 2H), 6.74 (d, J=8.8 Hz, 2H), 2.22 (s, 3H).

Workup

  1. additionwas added to pH=1
  2. filtrationThe yellow solid was filtered
  3. customrecrystallized out of toluene
  4. washwashed with hexane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d1eac5d8b4824bdbbe51f0da76fb8d66
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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