Hydrochloric Acid → HCID 16657516, compound

HRID 426076Notes

Reaction equation

HRID 426076 reaction equation
[OH-].[Na+].[OH:3][CH:4]([CH2:37][OH:38])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20]CC)=[O:19])=[CH:14][CH:13]=2)=[CH:8][C:7]=1[C:23]1[CH:32]=[CH:31][C:30]2[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:36])([CH3:35])[C:25]=2[CH:24]=1.Cl>O1CCCC1.C(O)C>[OH:3][CH:4]([CH2:37][OH:38])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([OH:20])=[O:19])=[CH:16][CH:17]=2)=[CH:8][C:7]=1[C:23]1[CH:32]=[CH:31][C:30]2[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:36])([CH3:35])[C:25]=2[CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66704109HCID 66704109, compound

Product 1

HCID 16657516HCID 16657516, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1 ml (1 mmol) of an aqueous solution of sodium hydroxide (1 M) is added to a solution of 200 mg (0.41 mmol) of ethyl 4′-(2,3-dihydroxypropyl)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)biphenyl-4-carboxylate in 5 ml of tetrahydrofuran and 2 ml of ethanol. The reaction mixture is stirred for 48 h while heating at 50° C. After the reaction mixture has returned to ambient temperature, 2 ml (2 mmol) of a solution of hydrochloric acid (1 N) are added. The medium is extracted with ethyl acetate. The organic phase is washed with water, and then dried over magnesium sulfate. After evaporation of the solvents, the product obtained is purified by crystallization from a heptane/diethyl ether mixture. 180 mg of 4′-(2,3-dihydroxypropyl)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)biphenyl-4-carboxylic acid are obtained (beige solid, Mp=145° C., yield=96%).

Workup

  1. customhas returned to ambient temperature
  2. extractionThe medium is extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvents
  6. customthe product obtained
  7. customis purified by crystallization from a heptane/diethyl ether mixture

Sources & evidence

ORD record
ord-88194e7f520f4ab885cc2c2605cfec75
Source dataset
uspto-grants-2012_01
Patent number
US08106235B2

Reaction notes

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