Methanol → HCID 178494498, compound

HRID 1419658Notes

Reaction equation

HRID 1419658 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH:22]=[O:23])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][C:5]=1[F:24].CO.[OH-].[Na+].O>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C@H:16]3[CH2:21][CH2:20][C@H:19]([CH:22]=[O:23])[CH2:18][CH2:17]3)[CH2:14][CH2:15]2)=[CH:6][C:5]=1[F:24]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 178494497HCID 178494497, compound

Product 1

HCID 178494498HCID 178494498, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.11 g of 4-[trans-4-(4-formylcyclohexyl)-cyclohexyl]-2-fluorobenzyl methyl ether (cis/trans=4:1) in 1.5 ml of methylene chloride was treated in succession with a few drops of triethylamine, 12 ml of methanol and 0.45 ml of 20 percent sodium hydroxide solution and stirred at room temperature for 30 minutes. Then, the reaction mixture was poured into 50 ml of water and extracted with methylene chloride. The organic phase was dried over sodium carbonate, filtered and the filtrate was evaporated. Crystallization from hexane gave 0.53 of pure 4-[trans-4-(trans-4-formylcyclohexyl)cyclohexyl]-2-fluorobenzyl methyl ether, m.p. 52°-54° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic phase was dried over sodium carbonate
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customCrystallization from hexane

Sources & evidence

ORD record
ord-fc8631225b1542e89e555828631150d7
Source dataset
uspto-grants-1999_03
Patent number
US05888423

Reaction notes

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