Hydrochloric Acid → 8-Hydroxy-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester

HRID 460962Notes

Reaction equation

HRID 460962 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[CH:7]=[CH:8][CH:9]=[C:10]([CH:12]=[O:13])[CH3:11])[CH3:2].[BH4-].[Na+].Cl>C(O)C>[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[CH2:12][OH:13])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoate

Product 1

HCID 539260748-Hydroxy-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

36 G. of 7-formyl-3-methyl-octa-2,4,6-trien-1oic acid ethyl ester are dissolved in 600 ml. of absolute ethanol. The solution is treated portionwise with 1.8 g. of sodium borohydride. The mixture is stirred for 2 hours at 10° C. then poured onto ice water and 3 N aqueous hydrochloric acid and extracted with ether. The ether extract is washed successively with water, a saturated aqueous sodium bicarbonate solution and once more with water, dried over sodium sulfate and evaporated. There is obtained 8-hydroxy-3,7-dimethyl-octa-2,4,6-trien-1-oic acid ethyl ester.

Workup

  1. additionThe solution is treated portionwise with 1.8 g
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed successively with water
  5. dry with materiala saturated aqueous sodium bicarbonate solution and once more with water, dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-4f0e1fc5ee104d7f91197d4de84b7083
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Reaction notes

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