Thionyl Chloride → HCID 19860606, compound

HRID 1165735Notes

Reaction equation

HRID 1165735 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30](O)=[O:31])=[CH:26][CH:25]=2)=[CH:20][C:19]=1[F:33])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>N1C=CC=CC=1>[CH2:5]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([Cl:3])=[O:31])=[CH:26][CH:25]=2)=[CH:20][C:19]=1[F:33])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 200435114'-Dodecyloxy-3'-fluorobiphenyl-4-carboxylic acid

Product 1

HCID 19860606HCID 19860606, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

Thionyl chloride (8.5 g) was added to 4.0 g of the 4'-dodecyloxy-3'-fluorobiphenyl-4-carboxylic acid synthesized by the method shown in Example 1, and one drop of pyridine was added. The mixture was refluxed for 6 hours. After the reaction, the reaction mixture was concentrated to obtain 4'-dodecyloxy-3'-fluorobiphenyl-4-carbonyl chloride. To the product was added 2.15 g of 4-hydroxyphenyl (s)-2-ethoxypropionate. Furthermore, 10 ml of dry pyridine was added, and the mixture was stirred at room temperature for 20 hours. After the reaction, the reaction mixture was poured into a large amount of ethyl acetate, and the mixture was washed twice with a dilute aqueous solution of hydrochloric acid, and three times with water. The ethyl acetate layer was dried over anhydrous sodium sulfate, and concentrated to give 6.05 g of crude crystals. The desired product was separated by silica gel chromatography using ethyl acetate/hexane as an eluent. Recrystallization from ethanol gave 4.01 g (yield 67%) of the desired product.

Workup

  1. customsynthesized by the method
  2. additionwas added
  3. temperatureThe mixture was refluxed for 6 hours
  4. customAfter the reaction
  5. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-0686e68628054d3fa3c482fd5cf4221a
Source dataset
uspto-grants-1990_03
Patent number
US04911862

Reaction notes

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