Hydrochloric Acid → HCID 68406476, compound

HRID 2098574Notes

Reaction equation

HRID 2098574 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH:12]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)=O.CC(OC(C)=O)=O.C(N(C(C)C)CC)(C)C.Cl>C(OCC)(=O)C.O>[CH3:21][O:20][C:18]([C:17]1[CH:22]=[CH:23][C:14]([CH:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:9]([OH:11])=[O:10])=[CH:15][CH:16]=1)=[O:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 15294Methyl 4-FormylbenzoateHCID 81531DiisopropylethylamineHCID 248474p-Tolylacetic acid

Product 1

HCID 68406476HCID 68406476, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 4-methylphenylacetic acid (3 g, 20 mmol) and methyl 4-formylbenzoate (3.3 g, 20 mmol) was dissolved under stirring with Ac2O (8 mL). To this mixture, diisopropylethylamine (DIPEA) (5.2 mL, 30 mmol) was added and stirred at 30° C. for 6 hours. Upon completion, as monitored by TLC using 100% ethyl acetate as eluent, the reaction mixture was poured into water and pH was adjusted to 3 using aqueous dilute HCl (1:1). The aqueous layer was extracted with ethyl acetate (2×150 mL). The combined ethyl acetate layer was washed with water till the washings were neutral and dried over anhydrous Na2SO4. The ethyl acetate layer was evaporated to dryness to obtain a sticky compound, which was triturated with cold dichloromethane (DCM) to furnish a pale yellow solid. It was filtered and dried under vacuum to afford the title compound (3.88 g, 66% yield).

Workup

  1. dissolutionwas dissolved
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×150 mL)
  3. washThe combined ethyl acetate layer was washed with water till the washings
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe ethyl acetate layer was evaporated to dryness
  6. customto obtain a sticky compound, which
  7. customwas triturated with cold dichloromethane (DCM)
  8. customto furnish a pale yellow solid
  9. filtrationIt was filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-cdbc94fda46744cfba4112aa05b97c76
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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