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

HRID 371547Notes

Reaction equation

HRID 371547 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-1-oic 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 3n 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, which is processed further as follows:

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-0d9ba1b67da942f4b85934d81f989ff6
Source dataset
uspto-grants-1985_07
Patent number
US04532355

Reaction notes

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