Methoxymethyl-triphenylphosphonium chloride → HCID 178459246, compound

HRID 2166815Notes

Reaction equation

HRID 2166815 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:24]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([CH:34]=O)[CH2:30][CH2:29]1)[CH2:25][CH3:26]>CCOCC>[CH3:2][O:3][CH:4]=[CH:34][C@H:31]1[CH2:30][CH2:29][C@H:28]([O:27][CH2:24][CH2:25][CH3:26])[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178459254HCID 178459254, compound

Product 1

HCID 178459246HCID 178459246, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of 94.6 g. of (methoxymethyl)triphenylphosphonium chloride in 1000 ml. of dry ether is treated with 33.0 g. of potassium tert.butylate. After stirring for 45 minutes, a solution of 31.4 g. of trans-4-n-propyloxycyclohexane carboxaldehyde in 200 ml. of ether is added dropwise. The mixture is stirred for a further 2.5 hours and then poured into 1.2 liters of ice-water. The organic phase is separated, washed neutral with water, dried over sodium sulfate and evaporated. The crude trans-2-(4-n-propyloxycyclohexyl)vinyl methyl ether obtained is distilled at 82°-85° C./0.6 mmHg in order to separate the residual triphenylphosphine.

Workup

  1. additionA suspension of 94.6 g
  2. stirringThe mixture is stirred for a further 2.5 hours
  3. customThe organic phase is separated
  4. washwashed neutral with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-9777017c8cd6415589d316c91aefc566
Source dataset
uspto-grants-1983_06
Patent number
US04389329

Reaction notes

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