Formic Acid → HCID 24754684, compound

HRID 1028928Notes

Reaction equation

HRID 1028928 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[CH2:14]O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.S(Cl)([Cl:24])=O.C(O)=O>C1C=CC=CC=1>[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[CH2:14][Cl:24])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 24386Thionyl ChlorideHCID 24754683HCID 24754683, compound

Product 1

HCID 24754684HCID 24754684, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
17.5 °C

Procedure

To a cooled solution of 3-[(p-Toluenesulfonyl)oxy]-4-methoxybenzyl alcohol 22 (8.0 g, 26 mmol) in benzene (25 mL) was added thionyl chloride (1.9 mL, 26 mmol) slowly over a period of 5-10 min maintaining the temperature around 15-20° C. The reaction was maintained at those conditions for 2 h and checked TLC for the completion. The flask is connected to a high vacuum through a trap containing formic acid under mild heating to remove excess thionyl chloride. The slurry formed after complete removal of thionyl chloride and benzene, filtered, washed with hexane and dried to afford 23. Yield: 90%; white solid mp 102-105° C. 1H NMR: δ 2.43 (s, 3H, CH3), 3.61 (s, 3H, OCH3), 4.50 (s, 2H, CH2), 6.80-7.79 (m, 7H, Ar—H). Anal. Calcd for C15H15ClO4S: C, 55.13, H, 4.63. Found: C, 53.20, H, 4.59.

Workup

  1. temperatureThe reaction was maintained at those conditions for 2 h
  2. customThe flask is connected to a high vacuum through a trap
  3. temperatureunder mild heating
  4. customto remove excess thionyl chloride
  5. customThe slurry formed
  6. customafter complete removal of thionyl chloride and benzene
  7. filtrationfiltered
  8. washwashed with hexane
  9. customdried

Sources & evidence

ORD record
ord-0a6fe2dbecd340e481520b458fe72461
Source dataset
uspto-grants-2014_05
Patent number
US08735620B2

Reaction notes

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