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

HRID 127753Notes

Reaction equation

HRID 127753 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.

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-174154e912584fe19b788ef2a3c21a98
Source dataset
uspto-grants-1981_03
Patent number
US04256878

Reaction notes

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