Ammonium Chloride → 1-Phenoxy-3-vinylbenzene

HRID 1069031Notes

Reaction equation

HRID 1069031 reaction equation
[Br-].C1([C:8]([PH3+])([C:15]2C=CC=CC=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)C=CC=CC=1.CC(C)([O-])C.[K+].[O:28](C1C=C(C=CC=1)C=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl-].[NH4+]>C1COCC1>[CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=1)=[CH2:15]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 382843-PhenoxybenzaldehydeHCID 21951224Triphenylmethyl phosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 98370411-Phenoxy-3-vinylbenzeneYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of triphenylmethylphosphonium bromide (25.23 g) and potassium tert-butoxide (1M solution in tetrahydrofuran) (75.67 ml) was stirred at 0° C. for 0.5 h. A solution of 3-phenoxy-benzaldehyde (10.0 g) in THF (10 ml) was added to the mixture and the reaction mixture stirred at 0° C. for 4 h. Ammonium chloride solution was added and the mixture extracted with diethyl ether. The organic extracts were combined, washed with water, dried and concentrated. Purification (SiO2, isohexane:ethyl acetate 4:1 as eluant) gave the subtitle compound (7.12 g).

Workup

  1. stirringthe reaction mixture stirred at 0° C. for 4 h
  2. extractionthe mixture extracted with diethyl ether
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customPurification (SiO2, isohexane:ethyl acetate 4:1 as eluant)

Sources & evidence

ORD record
ord-be9fb439323f43619c9e52c210405015
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

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