Sodium methanolate methanol → HCID 54218980, compound

HRID 1285027Notes

Reaction equation

HRID 1285027 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[C:16]([CH2:18][CH2:19][CH2:20]Br)[CH:15]=[CH:14][C:13]=2[C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32]Br)=[CH:26][C:25]=2[CH:34]2[CH2:39][CH2:38][CH:37]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:36][CH2:35]2)=[O:23])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:45][O-:46].[Na+].[CH3:48][OH:49]>CO>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[C:16]([CH2:18][CH2:19][CH2:20][O:46][CH3:45])[CH:15]=[CH:14][C:13]=2[C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][O:49][CH3:48])=[CH:26][C:25]=2[CH:34]2[CH2:39][CH2:38][CH:37]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:36][CH2:35]2)=[O:23])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 54446909HCID 54446909, compound

Product 1

HCID 54218980HCID 54218980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In another flask were placed 40 g of 4-pentylcyclohexyl-p-(3-bromopropyl)phenyl ketone and 200 ml of CH3OH and stirred. Thereafter, a sodium methylate-methanol solution prepared by dissolving 3.5 g of Na in 80 ml of absolute CH3OH was added thereto dropwise, and the resulting solution was refluxed. After 6 hours, the reaction solution was concentrated and then poured into water, after which the separated oil layer was extracted with benzene. After the benzene was distilled off, the residue was distilled under reduced pressure to obtain 4-pentylcyclohexyl-p-(3-methoxypropyl)phenyl ketone. The boiling point of this compound was 168°-171° C./0.08 mmHg.

Workup

  1. customIn another flask were placed
  2. additionwas added
  3. temperaturedropwise, and the resulting solution was refluxed
  4. concentrationthe reaction solution was concentrated
  5. additionpoured into water
  6. extractionafter which the separated oil layer was extracted with benzene
  7. distillationAfter the benzene was distilled off
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-9bf95c36c3a14a14a414d171a2d126f4
Source dataset
uspto-grants-1986_01
Patent number
US04564694

Reaction notes

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