Sodium Chloride → HCID 21899798, compound

HRID 719602Notes

Reaction equation

HRID 719602 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:26])[CH:7]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10].[Cl-].[Na+]>O.O1CCCC1.CO>[C:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:18]=[CH:19][C:14]([CH2:13][O:12][CH:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]([OH:26])=[O:5])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 69593273HCID 69593273, compound

Product 1

HCID 21899798HCID 21899798, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.0443 g, 1.056 mmol) in water (3 ml) was added drop-wise over 1 minute to a solution of 2-(biphenyl-4-ylmethoxy)-4-methyl-pentanoic acid methyl ester (0.11 g, 0.3521 mmol) in tetrahydrofuran:methanol 2:1 (15 ml) at 0° C. The mixture was stirred at ambient temperature for 16 hours then poured into saturated aqueous sodium chloride solution (10 ml). The aqueous layer was extracted with diethyl ether (2×10 ml) which was discarded. The aqueous layer was acidified with 1M hydrochloric acid to pH (1˜2), then the product was extracted into dichloromethane (3×10 ml). The combined dichloromethane layers were washed with water (2×10 ml), saturated aqueous sodium chloride solution (2×10 ml) then dried (Na2SO4) and the solvents removed in vacuo to leave 2-(biphenyl-4-ylmethoxy)-4-methyl-pentanoic acid as a colourless oil (0.048 g, 45.69%). TLC (single UV spot, Rf=0.2, methanol:dichloromethane 0.5:9.5), HPLC-MS (297.1 [M−1)+, 321.1 [M+Na]+, 619.3 [2M+Na]+).

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether (2×10 ml) which
  2. extractionthe product was extracted into dichloromethane (3×10 ml)
  3. washThe combined dichloromethane layers were washed with water (2×10 ml), saturated aqueous sodium chloride solution (2×10 ml)
  4. dry with materialthen dried (Na2SO4)
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-6ee7a70e512b43ddbf54758ca5ac429b
Source dataset
uspto-grants-2006_11
Patent number
US07132449B2

Reaction notes

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