Hydrochloric Acid → HCID 178447983, compound

HRID 1443610Notes

Reaction equation

HRID 1443610 reaction equation
C1(C)C=CC=CC=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:22]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32][C@H:33]2[CH2:38][CH2:37][C@H:36]([C:39](OCC)=[O:40])[CH2:35][CH2:34]2)[CH2:27][CH2:26]1)[CH2:23][CH3:24].Cl>C1(C)C=CC=CC=1>[CH2:22]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32][C@H:33]2[CH2:34][CH2:35][C@H:36]([CH2:39][OH:40])[CH2:37][CH2:38]2)[CH2:27][CH2:26]1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67340441Sodium bis(2-methoxyethoxy)aluminum hydride tolueneHCID 178447985HCID 178447985, compound

Product 1

HCID 178447983HCID 178447983, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 70% sodium bis(2-methoxyethoxy)aluminum hydride toluene solution (60.0 g) was added by titration to a toluene solution (100 mL) of ethyl trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexanecarboxylate (55.1 g), and thereafter, the resultant was continuously stirred until it cooled down to room temperature due to subdued heating. After the reaction was halted by adding ice water to a reaction solution, toluene was added, and concentrated hydrochloric acid was added until the dissolution of the deposited solid. An organic layer was separated and extracted with toluene from a water layer. Thus collected organic layer was washed by using water, a saturated sodium bicarbonate aqueous solution and brine in that order, and dried with anhydrous magnesium sulphate. Solvents were removed by distillation to obtain a slightly yellow solid of 47.3 g.

Workup

  1. additionwas added
  2. customAn organic layer was separated
  3. extractionextracted with toluene from a water layer
  4. washThus collected organic layer was washed
  5. dry with materiala saturated sodium bicarbonate aqueous solution and brine in that order, and dried with anhydrous magnesium sulphate
  6. customSolvents were removed by distillation
  7. customto obtain a slightly yellow solid of 47.3 g

Sources & evidence

ORD record
ord-32d1529998a8429a8996f5519db6f385
Source dataset
uspto-grants-2010_02
Patent number
US07662442B2

Reaction notes

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