Hydrochloric Acid → HCID 178455780, compound

HRID 2241794Notes

Reaction equation

HRID 2241794 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](OC)=[O:16])[CH2:11][CH2:10]1)=[CH2:8].O.Cl>C1COCC1>[CH:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][OH:16])[CH2:11][CH2:10]1)=[CH2:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178455792HCID 178455792, compound

Product 1

HCID 178455780HCID 178455780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
15 °C

Procedure

5.7 g of lithium aluminum hydride was dispersed in 50 mL of THF and all of methyl trans-4-vinylcyclohexanecarboxylate was dissolved in 75 mL of THF and then the resulting solution was added dropwise at 15 to 16° C. over 40 minutes. After stirring at 10 to 20° C. for 30 minutes, water was slowly added. About 70 mL of 10% hydrochloric acid was added and a sludge-like insoluble was removed by decantation, and then the resulting organic layer was washed with in turn with 10% hydrochloric acid, a saturated sodium hydrogen carbonate solution, and saturated saline. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain 26 g of (trans-4-vinylcyclohexyl)methanol.

Workup

  1. additionthe resulting solution was added dropwise at 15 to 16° C. over 40 minutes
  2. customa sludge-like insoluble was removed by decantation
  3. washthe resulting organic layer was washed with in turn with 10% hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ddc890fef2474e41b5f817a96d24f359
Source dataset
uspto-grants-2010_03
Patent number
US07670504B2

Reaction notes

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