Methanol → HCID 57541975, compound

HRID 922174Notes

Reaction equation

HRID 922174 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[CH3:6][OH:7].COC(=O)C(C1C=CC(OC[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:22]=2)=CC=1)C.[OH-:36].[Na+]>O>[C:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:3][O:4][C:5]1[CH:1]=[CH:2][C:22]([CH2:23][CH2:24][C:6]([OH:36])=[O:7])=[CH:21][CH:26]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66686028HCID 66686028, compound

Product 1

HCID 57541975HCID 57541975, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 100 mL RB flask fitted with magnetic stirrer was charged 15 mL of THF, 1.0 mL water, and 1.0 mL methanol. To the stirred solvent mixture was added [4-(3-benzoyl-benzyloxy)-phenyl]-propanoic acid methyl ester (1.5 g, 4.0064 mmol) followed by the addition of sodium hydroxide (0.480 g, 12.02 mmol). The resulting solution was stirred at RT for 15 h. After completion of the reaction (reaction monitored by TLC), RM was diluted with 10 mL of water and washed with 40 mL DCM (50 mL×2). Then the aqueous layer was acidified to pH 6 using conc. HCl and extracted with DCM (75 mL×3). The DCM layer was washed with water (75 mL), dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as white solid (1.4 g, yield: 97.2%): MS (ESI, 120 eV): m/z=361.1 (M+H)+: 1H NMR (300 MHz, CDCl3): δ 12.09 (s, 1H), 7.80 (s, 1H), 7.66-7.73 (m, 5H), 7.56-7.58 (d, 3H), 7.13-7.16 (m, 2H), 6.90-6.93 (d, 2H), 5.18 (s, 2H), 2.72-2.77 (t, 2H), 2.42-2.45 (m, 2H).

Workup

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction monitored by TLC), RM
  3. washwashed with 40 mL DCM (50 mL×2)
  4. extractionextracted with DCM (75 mL×3)
  5. washThe DCM layer was washed with water (75 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e15a283fbcf644728844b7691f04c088
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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