Hydrochloric Acid → (R)-3-(4-Methoxybenzyloxy)tetradecanoic acid

HRID 1022290Notes

Reaction equation

HRID 1022290 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][C@H:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:10][C:11]([O:13]C)=[O:12])=[CH:5][CH:4]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.CC#N.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C@H:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:10][C:11]([OH:13])=[O:12])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59611709(R)-Methyl 3-(4-methoxybenzyloxy)tetradecanoate

Product 1

HCID 16216483(R)-3-(4-Methoxybenzyloxy)tetradecanoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 67586856THF MeOH CH3CNSolvent

Procedure

Ester 32 (4.01 g, 10.4 mmol) was dissolved in THF/MeOH/CH3CN mixture (v/v/v, 1/1/1, 90 mL). Lithium hydroxide monohydrate (874 mg, 20.8 mmol) as a solution in water (30 mL) was added, and the mixture stirred overnight. The solvent amount was reduced in vacuo to about 30 mL. To the remaining aqueous solution was added hydrochloric acid (1 M) to bring the pH down to 3. The aqueous layer was extracted with diethyl ether (3×40 mL). The combined organic extracts were dried over sodium sulfate. The drying agent was removed by filtration and the solvents removed using a rotary evaporator. The residue was purified by chromatography on silica gel (120 g RediSep column, eluting with a gradient of 0% through 50% ethyl acetate/hexanes over 60 min, 85 mL/min) to give the product 34 (3.37 g, 89%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) δ 7.22 (d, J=6.1 Hz, 2H), 6.82 (d, J=6.1 Hz, 2H), 4.46 (s, 2H), 3.81 (m, 1H), 3.75 (s, 3H), 2.65-2.49 (m, 2H), 1.80-1.60 (m, 2H), 1.50-1.20 (m, 18H), 0.85 (t, J=5.8 Hz, 3H).

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether (3×40 mL)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe solvents removed
  5. customa rotary evaporator
  6. customThe residue was purified by chromatography on silica gel (120 g RediSep column
  7. washeluting with a gradient of 0% through 50% ethyl acetate/hexanes over 60 min

Sources & evidence

ORD record
ord-c3bc762d910c42d4a6430e2c52407dd2
Source dataset
uspto-grants-2014_05
Patent number
US08722064B2

Reaction notes

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