Hydrochloric Acid → (R)-3-(Benzyloxy)tetradecanoic acid

HRID 1022288Notes

Reaction equation

HRID 1022288 reaction equation
[CH2:1]([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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.CC#N.O>[CH2:1]([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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 13817922Methyl (3R)-3-(benzyloxy)tetradecanoate

Product 1

HCID 11110428(R)-3-(Benzyloxy)tetradecanoic acidYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 67586856THF MeOH CH3CNSolvent

Procedure

Ester 31 (1.3 g, 3.73 mmol) was dissolved in THF/MeOH/CH3CN mixture (v/v/v, 1/1/1, 90 mL). Lithium hydroxide monohydrate (235 mg, 5.6 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 1 M hydrochloric acid 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 (40 g RediSep column, eluting with a gradient of 0% through 50% ethyl acetate/hexanes over 40 min, 40 mL/min) to give the product 33 (990 mg, 79%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) δ 7.30-7.05 (m, 5H), 4.51 (s, 2H), 3.90-3.80 (m, 1H), 2.58-2.45 (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 (40 g RediSep column
  7. washeluting with a gradient of 0% through 50% ethyl acetate/hexanes over 40 min

Sources & evidence

ORD record
ord-f9185157669443ddb1457666cc20bb43
Source dataset
uspto-grants-2014_05
Patent number
US08722064B2

Reaction notes

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