HCID 70414754, compound → HCID 70350596, compound

HRID 868429Notes

Reaction equation

HRID 868429 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([C:19]1[C:24]([CH:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=[CH:21][C:20]=1[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]([OH:45])[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:34]=1[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:12]([C:19]1[C:24]([C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=[CH:21][C:20]=1[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39](=[O:45])[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:34]=1[CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70414754HCID 70414754, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 70350596HCID 70350596, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of pyridinium chlorochromate (32.3 g) in methylene chloride (200 ml) was added a solution of benzyl-3-[1-hydroxyhexyl]phenyl ether (28.4 g.) in methylene chloride (25 ml). The reaction was stirred at room temperature for 11/2 hours. The excess methylene chloride was decanted and residual black solid was triturated with ethyl ether (four times.) The combined organic extract was purified on flurosil using ethyl ether as an eluent (27.5 g., 98% yield).

Workup

  1. customThe excess methylene chloride was decanted
  2. customresidual black solid was triturated with ethyl ether (four times.) The combined
  3. extractionorganic extract
  4. customwas purified on flurosil

Sources & evidence

ORD record
ord-4d47eb5675fd416ebcca0a367fb4a149
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

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