Hydrochloric Acid → HCID 14651073, compound

HRID 1607174Notes

Reaction equation

HRID 1607174 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH2:3]1.CCOCC.[F:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1.Cl>O1CCCC1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:4]2([OH:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2]([CH3:11])([CH3:1])[CH2:3]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 843993,3,5,5-TetramethylcyclohexanoneHCID 178418676HCID 178418676, compound

Product 1

HCID 14651073HCID 14651073, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 51.42g (333.3 mmoles) of 3,3,5,5-tetramethylcyclohexanone in 200 ml of tetrahydrofuran (THF) was added dropwise to an ice cold solution made up of 200 ml of a 2M ether solution of 4-fluorophenyl magnesium bromide (400 mmoles) and 100 ml of THF. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was then poured onto ice and 500 ml of 1N HCl. After stirring for 0.5 hour, the layers were separated. The aqueous layer was extracted once with ether and the combined organic layers were evaporated in vacuo to obtain the title compound in the form of an oil.

Workup

  1. stirringAfter stirring for 0.5 hour
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted once with ether
  4. customthe combined organic layers were evaporated in vacuo

Sources & evidence

ORD record
ord-ce035f9358b34e358f84556dda4fd482
Source dataset
uspto-grants-1989_09
Patent number
US04863957

Reaction notes

Loading…