Sodium Hydroxide → HCID 68775456, compound

HRID 1175598Notes

Reaction equation

HRID 1175598 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:16])([CH3:15])[C:10]([O:12]CC)=[O:11])[CH:6]=[CH:5][C:4]=1[C:17]1[CH:22]=[C:21]([CH2:23][O:24][CH3:25])[CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:16])([CH3:15])[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][C:4]=1[C:17]1[CH:22]=[C:21]([CH2:23][O:24][CH3:25])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68776168HCID 68776168, compound

Product 1

HCID 68775456HCID 68775456, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(2-methoxy-5′-(methoxymethyl)biphenyl-4-yl)-2-methylpropanoate (example 27b) (986 mg, 2.88 mmol) was suspended in EtOH (10 mL) and 1M aq. NaOH (15 mL) and stirred at 100° C. for 3 h. EtOH was removed under reduced pressure and the residue was diluted with water (10 mL) and acidified with 6N aq. HCl to pH 2-3. The product was extracted with EtOAc, washed with water and brine, dried over MgSO4, filtered and evaporated to give 900 mg (99%) of 2-(2-Methoxy-5′-(methoxymethyl)biphenyl-4-yl)-2-methylpropanoic acid. 1H NMR(400 MHz, DMSO): δ 1.48 (s, 6H), 3.29 (s, 3H), 4.45 (s, 2H), 7.40-7.61 (m, 8H), 12.44 (s, 1H).

Workup

  1. customEtOH was removed under reduced pressure
  2. additionthe residue was diluted with water (10 mL)
  3. extractionThe product was extracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-eca29017e6d34e5285c8ca4aa647999d
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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