Hydrochloric Acid → HCID 21717629, compound

HRID 1386478Notes

Reaction equation

HRID 1386478 reaction equation
[CH3:1][C:2]1[C:3]([CH:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH:17]=[CH2:18])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[OH-:27].[K+].Cl.[OH2:30]>>[CH3:1][C:2]1[C:3]([CH:16]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[CH:17]=[CH2:18])=[CH:4][C:5]2[C:6]([CH3:14])([CH3:15])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1.[CH3:1][C:2]1[C:3]([CH:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]([OH:30])=[O:27])=[CH:21][CH:20]=2)[CH:17]=[CH2:18])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 21717629HCID 21717629, compound

Product 2

HCID 21717629HCID 21717629, compoundHCID 21717637HCID 21717637, compound

Conditions

Temperature
70 °C

Procedure

A suspension of the derivative (E) 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2-propenyl]benzonitrile (0.22 g, 0.64 mmol) prepared previously in alcoholic potassium hydroxide (0.94 g, 16.8 mmol KOH in 0.55 ml H2O and 3.3 ml EtOH) is heated to 70° C. under magnetic stirring for 6 hours. The progress of the reaction is followed by HPLC. After cooling of the reaction medium, it is taken up in water (50 ml), acidified by 1N HCl, extracted with ether (4×20 ml) and the ether phase dried with MgSO4, filtered and evaporated to obtain a raw product which is purified by washing with hexane. After drying at 50° C. (3 hours) in a desiccator under vacuum, 0.18 g of a whitish product, the acid (E) pure 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2-propenyl]benzoic acid is obtained (yield=75%).

Workup

  1. temperatureAfter cooling of the reaction medium, it
  2. extractionextracted with ether (4×20 ml)
  3. dry with materialthe ether phase dried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto obtain a raw product which
  7. customis purified
  8. washby washing with hexane
  9. dry with materialAfter drying at 50° C. (3 hours) in a desiccator under vacuum, 0.18 g of a whitish product

Sources & evidence

ORD record
ord-c8a3ee87e9604824bf7961a0da9d69cb
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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