Methanol → HCID 67515890, compound

HRID 2173333Notes

Reaction equation

HRID 2173333 reaction equation
[Li+].[OH-].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14]CC)=[O:13])=[CH:7][C:6]=1[O:17][CH3:18])#[N:4].CO>C1COCC1>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[O:17][CH3:18])#[N:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66643843Ethyl 2-(4-cyano-3-methoxyphenyl)acetate

Product 1

HCID 67515890HCID 67515890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous LiOH (0.096 g, 2.9 mmol, in 2 mL of water) was added to a stirred solution of ethyl (4-cyano-3-methoxyphenyl)acetate (0.50 g, 2.9 mmol) in THF:CH3OH) 5:1 (23 mL), and the solution was stirred at room temperature overnight. After acidification to pH 3 with 1 N HCl, the aqueous was extracted with AcOEt (2×50 mL). The organic phase was washed with brine, dried (MgSO4), and evaporated under reduced pressure to give the (4-cyano-3-methoxyphenyl) acetic acid, which was used in the next step without further purification. NMR (500 MHz, DMSO-d6), δ 12.52 (s, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.17 (s, 1H), 7.0 (d, J=7.8.0 Hz, 1H), 3.89 (s, 3H), 3.69 (s, 2H); LC/MS (M+1)+=192.16; tR=0.52 min.

Workup

  1. extractionAfter acidification to pH 3 with 1 N HCl, the aqueous was extracted with AcOEt (2×50 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ca64354e8c95421a86864327c8afd3bc
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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