Thionyl Chloride → 3-(1-Adamantyl)-4-methoxybenzoyl chloride

HRID 249024

Reaction equation

HRID 249024 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[C:14](O)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)([Cl:24])=O>>[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[C:14]([Cl:24])=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid

Product 1

HCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chlorideYield 100%

Procedure

In a round bottom flask, there are introduced 200 ml of thionyl chloride and there are then added, in small fractions, 35 g (122 mmoles) of the acid obtained in stage (a), above. The reaction mixture is heated to reflux until the emission of gases ceases. The reaction mixture is evaporated to dryness, taken up in 100 ml of anhydrous benzene and again evaporated to dryness, yielding 37 g of the expected product (100% yield) having a melting point of 153°-154° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux until the emission of gases ceases
  3. customThe reaction mixture is evaporated to dryness
  4. customagain evaporated to dryness

Sources & evidence

ORD record
ord-19110497a281468ea9a9a7cea488f338
Source dataset
uspto-grants-1993_05
Patent number
US05212203

Linked notes

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