Thionyl Chloride → Hexahydro-2,5-methano-pentalene-3a-carbonyl chloride

HRID 76248

Reaction equation

HRID 76248 reaction equation
[CH2:1]1[CH:6]2[CH2:7][C:8]3([C:10]([OH:12])=O)[CH2:9][CH:2]1[CH2:3][CH:4]3[CH2:5]2.O=S(Cl)[Cl:15]>C1(C)C=CC=CC=1>[CH2:5]1[CH:4]2[C:8]3([C:10]([Cl:15])=[O:12])[CH2:9][CH:2]([CH2:1][CH:6]1[CH2:7]3)[CH2:3]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acid

Product 1

HCID 13182402Hexahydro-2,5-methano-pentalene-3a-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Noradamantane carboxylic acid (4.99 g, 30.1 mmol) and SOCl2 (5 mL, 69 mmol) in toluene (5 mL) were heated to 65° C. until vigorous evolution of gas commenced. The heating bath was removed for 5-10 minutes until gas evolution had moderated. Heating the reaction again at 65° C. was resumed for 2 hours. The reaction was cooled to room temperature, the volatiles removed in vacuo and toluene added and evaporated (2×) to remove excess SOCl2. The crude acid chloride was used without further purification.

Workup

  1. customThe heating bath was removed for 5-10 minutes until gas evolution
  2. temperatureHeating
  3. customthe reaction again at 65° C.
  4. customthe volatiles removed in vacuo and toluene
  5. additionadded
  6. customevaporated (2×)
  7. customto remove excess SOCl2
  8. customThe crude acid chloride was used without further purification

Sources & evidence

ORD record
ord-ca9fc7d8aa2b4d27a2f2cc662805fc08
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Linked notes

Loading…