Hydrochloric Acid → HCID 53926074, compound

HRID 27867Notes

Reaction equation

HRID 27867 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 53926074HCID 53926074, compound

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 3 n aqueous hydrochloric acid and extracted with ether. The ether extract is washed successively with water, a saturated aqueous sodium bicarbonate sodium 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 sodium and once more with water, dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-cc9bee96907546cab6b85a562360d591
Source dataset
uspto-grants-1980_09
Patent number
US04224244

Reaction notes

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