Hydrochloric Acid → HCID 67295236, compound

HRID 1773852Notes

Reaction equation

HRID 1773852 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:10][C:11]1([CH2:26][C:27](O)=[O:28])[CH2:16][CH2:15][CH:14]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)(O)=[O:8].O.Cl>C1COCC1>[OH:8][CH2:7][CH2:10][C:11]1([CH2:26][CH2:27][OH:28])[CH2:16][CH2:15][CH:14]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67295308HCID 67295308, compound

Product 1

HCID 67295236HCID 67295236, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.0 g (0.26 mol) of lithium aluminium hydride are suspended in 200 ml of THF, and a solution of 24.0 g (74.0 mmol) of (4-carboxymethyl-4′-propylbicyclohexyl-4-yl)acetic acid in 300 ml of THF is metered in. When the addition is complete, the mixture is stirred at RT for 1 h and at the reflux temperature for 3 h. The reaction mixture is hydrolysed using water and neutralised using dil. hydrochloric acid. The salts are filtered off, and the filtrate is diluted with MTBE. The solution is washed with saturated sodium chloride solution and dried using sodium sulfate. The solid remaining after removal of the solvents is recrystallised from acetonitrile, giving 2-[4-(2-hydroxyethyl)-4′-propylbicyclohexyl-4-yl]ethanol as a beige solid.

Workup

  1. additionWhen the addition
  2. filtrationThe salts are filtered off
  3. additionthe filtrate is diluted with MTBE
  4. washThe solution is washed with saturated sodium chloride solution
  5. customdried
  6. customafter removal of the solvents
  7. customis recrystallised from acetonitrile

Sources & evidence

ORD record
ord-c4a0e03b8024426e9914c86fc35ec579
Source dataset
uspto-grants-2016_02
Patent number
US09255223B2

Reaction notes

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