Hydrochloric Acid → HCID 87206546, compound

HRID 1851866Notes

Reaction equation

HRID 1851866 reaction equation
CC([S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Br:17])=O.C([O-])([O-])=O.[K+].[K+].Cl>>[SH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Br:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86186175HCID 86186175, compound

Product 1

HCID 87206546HCID 87206546, compound

Procedure

Alternations to the referenced procedure include the substitution of S-12-(2,5-dihydroxyphenyl)dodecyl ethanethioate with CH3(CO)S(CH2)12Br and K2CO3 for concentrated HCl, the reaction time was reduced from 12 h to 5 h and the product was purified by sublimation (−20° C. cold finger, 0.5 mmHg, 70° C. oil bath). Yield; 3.47 g, 12.32 mmol, 89%; 1H NMR (400.09 MHz, CDCl3) δ (ppm); 3.40 (t, 2H, 3JH—H=7.2 Hz, BrCH2), 2.51 (dt, 2H, 3JH—H=7.2 Hz, HSCH2), 1.84 (quintet, 2H, 3JH—H=7.2 Hz, BrCH2CH2), 1.60 (quintet, 2H, 3JH—H=7.2 Hz, HSCH2CH2), 1.44-1.26 (m, 17H, CH2 and SH t, 3JH—H=7.6 Hz). 13C NMR (100.60 MHz, CDCl3) δ (ppm); 45.14, 34.01, 32.80, 32.61, 29.45, 29.03, 28.85, 28.72, 28.33, 28.14, 26.84, 24.62.

Workup

  1. waitthe reaction time was reduced from 12 h to 5 h
  2. customthe product was purified by sublimation (−20° C. cold finger, 0.5 mmHg, 70° C. oil bath)

Sources & evidence

ORD record
ord-0b709ad1d4d04219b1bca48a8c266ac6
Source dataset
uspto-grants-2015_02
Patent number
US08957243B2

Reaction notes

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