Hydrochloric Acid → HCID 10111138, compound

HRID 1836876Notes

Reaction equation

HRID 1836876 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:21]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:20][C:19]3[C:18]([CH3:27])([CH3:26])[CH2:17][CH2:16][C:15]([CH3:29])([CH3:28])[C:14]=3[CH:13]=2)=[CH:6][CH:5]=1.[Li+].[OH-].Cl>CO.C(OCC)C>[OH:25][CH2:24][CH2:23][CH2:22][C:21]1[C:12](/[CH:11]=[CH:10]/[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[CH:5][CH:6]=2)=[CH:13][C:14]2[C:15]([CH3:29])([CH3:28])[CH2:16][CH2:17][C:18]([CH3:26])([CH3:27])[C:19]=2[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23498888HCID 23498888, compound

Product 1

HCID 10111138HCID 10111138, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 27.0 g (0.66 mmol) of Methyl-4-{(E)-2-[3-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate in 10 mL of methyl alcohol was added 5 mL of 1 N LiOH. The reaction mixture was heated to reflux. After 4 hours, the reaction mixture was cooled to room temperature, diluted with diethyl ether and acidified with concentrated HCl. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by crystallization (hexane/ethyl acetate) to give 200 mg (76%) of 4-{(E)-2-[3-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoic acid (m.p.: 212.8-213.2° C.) 12.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by crystallization (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fd7864ce434148fea97ab7b775b3e8dd
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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