Bis(Chloromethyl) Ether → HCID 21274965, compound

HRID 1382648Notes

Reaction equation

HRID 1382648 reaction equation
Cl[CH2:2][O:3][CH2:4]Cl.[OH-].[Na+].[C:8]1([CH:14]([C:30]([F:33])([F:32])[F:31])[CH:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1C=CC=CC=1>[C:8]1([CH:14]([C:30]([F:33])([F:31])[F:32])[CH:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:2][O:3][CH3:4])=[CH:20][CH:21]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10967Bis(Chloromethyl) EtherHCID 14798Sodium HydroxideHCID 21274953HCID 21274953, compound

Product 1

HCID 21274965HCID 21274965, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

9.6 g (120 mmoles) of chloromethyl ether and 8.4 g (210 mmoles) of powdered sodium hydroxide are added to a solution of 27.7 g (76 mmoles) of 2-phenyl-3,3,3-trifluoro-1-(4-fluorophenyl)-1-(4-hydroxyphenyl)-propane in 100 ml of benzene, prepared as described in Example 22, and the mixture is boiled for one hour. The reaction mixture is diluted with 150 ml of benzene, washed with a 20% aqueous ammonium chloride solution until neutral, dried and evaporated. The residue is dissolved in benzene and passed through a chromatographic column filled with 650 g of silica gel. The first eluate fractions are combined and evaporated to obtain 20.66 g (66.6%) of 2-phenyl-3,3,3-trifluoro-1-(4-fluorophenyl)-1-(4-methoxymethoxy-phenyl)-propane, which is applied in the subsequent step without purification.

Workup

  1. customprepared
  2. washwashed with a 20% aqueous ammonium chloride solution until neutral,
  3. customdried
  4. customevaporated
  5. dissolutionThe residue is dissolved in benzene
  6. additionfilled with 650 g of silica gel
  7. customevaporated

Sources & evidence

ORD record
ord-4a6ed37ebcda4f769522b97b7fc45d6c
Source dataset
uspto-grants-1989_02
Patent number
US04806685

Reaction notes

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