Sodium Hydroxide → HCID 10404777, compound

HRID 48313Notes

Reaction equation

HRID 48313 reaction equation
C([O:3][C:4](=[O:23])[C:5]([CH3:22])([CH3:21])[CH2:6][CH2:7][CH2:8][S:9][CH2:10][S:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])C.[OH-].[Na+]>C(O)C.O>[CH3:21][C:5]([CH3:22])([CH2:6][CH2:7][CH2:8][S:9][CH2:10][S:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])[C:4]([OH:23])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 879781612,2,12,12-Tetramethyl-6,8-dithiatridecane-1,13-dioic acid ethyl ester

Product 1

HCID 10404777HCID 10404777, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2,2,12,12-tetramethyl-6,8-dithiatridecane-1,13-dioic acid ethyl ester (7.16 g, 18.25 mmol) and sodium hydroxide (3.13 g, 76 mmol) in ethanol (40 mL) and deionized water (4 mL) was heated to reflux for 2 h. The ethanol was evaporated and the residue dissolved in water (30 mL) and extracted with diethyl ether (20 mL). The aqueous layer was acidified with 2 N hydrochloric acid to pH 2 and extracted with diethyl ether (2×20 mL). The combined organic layers were washed with saturated sodium chloride solution (15 mL), dried over MgSO4, and concentrated to give the crude product (4.79 g) as an oil, which solidified on standing. Recrystallization (hexanes/ethyl acetate=2/1) yielded 2,2,12,12-tetramethyl-6,8-dithiatridecane-1,13-dioic acid (2.9 g, 47%) as nice white needles. Mp.: 72.0-72.5° C.). 1H NMR (300 MHz, CDCl3/TMS): d (ppm): 11.55 (br, 2H), 3.65 (s, 2H), 2.62 (t, J=6.8 Hz, 4H), 1.70-1.51 (m, 8H), 1.21 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): d (ppm): 184.76, 41.99, 39.54, 35.20, 31.07, 24.87, 24.54. HRMS (HR, LSIMS, gly): Calcd. for C15H29O4S2 (MH+): 337.1507, found 337.1508. Anal. (C15H28O4S2) calcd. (found): C, 53.54 (53.38); H, 8.39 (8.26); S, 19.06 (19.29).

Workup

  1. temperatureto reflux for 2 h
  2. customThe ethanol was evaporated
  3. dissolutionthe residue dissolved in water (30 mL)
  4. extractionextracted with diethyl ether (20 mL)
  5. extractionextracted with diethyl ether (2×20 mL)
  6. washThe combined organic layers were washed with saturated sodium chloride solution (15 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customto give the crude product (4.79 g) as an oil, which
  10. customRecrystallization (hexanes/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-116cc91ad47e4e078c15e99bec9fd0bd
Source dataset
uspto-grants-2004_03
Patent number
US06703422B2

Reaction notes

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