Hydrochloric Acid → HCID 53258796, compound

HRID 451356Notes

Reaction equation

HRID 451356 reaction equation
[CH2:1]([C:14]1[C:15]2[S:24][C:23](CC)=[C:22]([Br:27])[C:16]=2[S:17][C:18]=1[C:19]([O-:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C1COCC1.[Li+].[OH-].Cl>O.CO>[CH2:1]([C:14]1[C:15]2[S:24][CH:23]=[C:22]([Br:27])[C:16]=2[S:17][C:18]=1[C:19]([OH:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86652861HCID 86652861, compound

Product 1

HCID 53258796HCID 53258796, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Tridecyl-6-bromo-thieno[3,2-b]thiophene-2-carboxylic acid (154) was prepared using the following procedure. Compound 153 (71.0 g, 0.15 mol) was dissolved into a mixture of THF (400 mL), methanol (50 mL), and LiOH (72 mL, 10% solution). This mixture was refluxed overnight and poured into concentrated hydrochloric acid (300 mL). The acid mixture was then diluted to 1000 mL with water. Solid was filtrated and washed with water (3×500 mL). The light yellow solid was washed with methanol (300 mL) and dried under vacuum overnight (46.40 g. 69.5%). Mp: 88-90° C. 1H NMR (300 MHz, CD2Cl2) δ 7.55 (s, 1H), 3.17 (t, 2H), 1.75 (t, 2H), 1.26 (m, 20H), 0.87 (t, 3H).

Workup

  1. temperatureThis mixture was refluxed overnight
  2. filtrationSolid was filtrated
  3. washwashed with water (3×500 mL)
  4. washThe light yellow solid was washed with methanol (300 mL)
  5. customdried under vacuum overnight (46.40 g. 69.5%)

Sources & evidence

ORD record
ord-bc0d93d33df1411f8d750434e0c52b9d
Source dataset
uspto-grants-2013_07
Patent number
US08487114B2

Reaction notes

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