Pentadecanoic Acid → Pentadecanoyl chloride

HRID 1953925Notes

Reaction equation

HRID 1953925 reaction equation
S(Cl)([Cl:3])=O.[C:5]([OH:21])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1(C)C=CC=CC=1>[C:5]([Cl:3])(=[O:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 13849Pentadecanoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 263097Pentadecanoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

C 18 resin: Pentadecanoyl chloride was synthesized by reacting 10 ml of 2 M thionyl chloride in 10 ml of toluene with 1.5 gm pentadecanoic acid. After 40 minutes of refluxing, the remaining thionyl chloride and toluene were removed by distillation. 4 gm of the 3-amino-propyl resin was then incubated overnight with the freshly prepared pentadecanoyl chloride in pyridine. The next day, the resin was twice washed with methylene chloride and then three times more with methanol and dried.

Workup

  1. temperatureAfter 40 minutes of refluxing
  2. customthe remaining thionyl chloride and toluene were removed by distillation
  3. washThe next day, the resin was twice washed with methylene chloride
  4. dry with materialthree times more with methanol and dried

Sources & evidence

ORD record
ord-d0cfdd032eed4c3b97c2047641393aec
Source dataset
uspto-grants-2000_09
Patent number
US06119699

Reaction notes

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