Hydrochloric Acid → HCID 59253932, compound

HRID 2405192Notes

Reaction equation

HRID 2405192 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][C:18]([O:20]C)=[O:19])[CH:12]=2)[CH:7]=1)[CH3:5].Cl>[OH-].[Na+]>[C:18]([CH2:17][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH:4]([CH3:5])[C:3]([OH:22])=[O:2])[CH:15]=[CH:14]2)([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59253984HCID 59253984, compound

Product 1

HCID 59253932HCID 59253932, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(6-Methoxycarbonylmethoxy-naphthalen-2-yl)-propionic acid methyl ester 31 (23 grams, 76.16 mmol) in 4 N—NaOH solutions (230 mL) was heated on a water bath at 90° C. for 8 hours. The reaction mass was cooled to room temperature and the pH adjusted to 2 with concentrated hydrochloric acid. Crude 89 was filtered, dried, and recrystallized from a mixture of ethyl acetate:hexane (1:6) to give pure 89 (15 grams, 71.9%) as a white powder. Mp: 185-188° C. IH NMR (DMSO-d6) δ 1.54(d,3H,CH3), 3.80(q,1H,CH), 4.74(s,2H,OCH2), 7.08(s,1H,Ar), 7.22(m,1H,Ar), 7.42(m,1H,Ar), 7.66(m,3H,Ar).

Workup

  1. temperatureThe reaction mass was cooled to room temperature
  2. filtrationCrude 89 was filtered
  3. customdried
  4. customrecrystallized from a mixture of ethyl acetate:hexane (1:6)

Sources & evidence

ORD record
ord-5bec20419a1b477ab893dc4b6acf2f24
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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