Diethyl Ether → 8-Bromo-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester

HRID 27868Notes

Reaction equation

HRID 27868 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[CH:7]=[CH:8][CH:9]=[C:10]([CH3:13])[CH2:11]O)[CH3:2].CCOCC.P(Br)(Br)[Br:22]>N1C=CC=CC=1.CCCCCC>[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[CH:7]=[CH:8][CH:9]=[C:10]([CH3:13])[CH2:11][Br:22])[CH3:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 539260748-Hydroxy-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester

Product 1

HCID 536327178-Bromo-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

36.5 g. of 8-hydroxy-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester are dissolved in 380 ml. of ether. The solution is cooled to 0° C., and after the addition of 3 drops of pyridine treated dropwise with 28.6 g. of phosphorous tribromide in 120 ml. of hexane. The mixture is stirred for 20 minutes at 0° C., then poured onto ice water and extracted with ether. The ether extract is washed successively with water, a saturated aqueous sodium bicarbonate solution and again with water, dried over sodium sulfate and evaporated. There is obtained 8-bromo-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester, which is processed as follows:

Workup

  1. additiontreated dropwise with 28.6 g
  2. additionpoured onto ice water
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washis washed successively with water
  6. dry with materiala saturated aqueous sodium bicarbonate solution and again with water, dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-005326eae1dd4681a79e7a3d00aa2b4b
Source dataset
uspto-grants-1980_09
Patent number
US04224244

Reaction notes

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