Dichloromethane → HCID 178455778, compound

HRID 1674442Notes

Reaction equation

HRID 1674442 reaction equation
ClCCl.[F:4][C:5]1[C:10]([F:11])=[C:9]([O:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][CH3:21])[CH2:16][CH2:15]2)[CH:8]=[CH:7][C:6]=1[OH:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CS(O[CH2:36][C@H:37]1[CH2:42][CH2:41][C@H:40]([CH:43]=[CH2:44])[CH2:39][CH2:38]1)(=O)=O>C1(C)C=CC=CC=1.O>[F:4][C:5]1[C:10]([F:11])=[C:9]([O:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH:20]=[CH2:21])[CH2:16][CH2:15]2)[CH:8]=[CH:7][C:6]=1[O:22][CH2:36][C@H:37]1[CH2:42][CH2:41][C@H:40]([CH2:43][CH3:44])[CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 178455779HCID 178455779, compoundHCID 178455794HCID 178455794, compound

Product 1

HCID 178455778HCID 178455778, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

In the dichloromethane (50 mL) solution containing 10 g of 2,3-difluoro-4-(trans-4-ethylcyclohexyl)methoxyphenol, 12 g of tripotassium phosphate and 8.1 g of (trans-4-vinylcyclohexyl)methyl methanesulfonate were dissolved, and the solution was stirred at 80 to 100° C. for 2 hours. Water and toluene were added to the solution, and the organic layer was fractioned, washed with water and saturated saline, and then dried over silicagel. The solvent was evaporated under reduced pressure. The residue was purified by recrystallization and column chromatography, to thereby obtain 7.9 g of 2,3-difluoro-1-(trans-4-ethylcyclohexyl)methoxy-4-(trans-4-vinylcyclohexyl)methoxybenzene (1b) in the form of colorless crystals.

Workup

  1. dissolutionwere dissolved
  2. washwashed with water and saturated saline
  3. customdried over silicagel
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by recrystallization and column chromatography

Sources & evidence

ORD record
ord-6841cf8f44b64655b131b9b248a074c2
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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