Sodium Hydroxide → HCID 13243718, compound

HRID 1702170Notes

Reaction equation

HRID 1702170 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[C:23](/[CH3:30])=[CH:24]\[C:25](OCC)=[O:26])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>CCOCC.O>[CH2:16]([O:15][C:13]1[CH:12]=[C:11]([CH:23]([CH3:30])[CH2:24][CH2:25][OH:26])[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 70530972HCID 70530972, compound

Product 1

HCID 13243718HCID 13243718, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3-(3,5-dibenzyloxyphenyl)crotonate (24.1 g., 60 mM) in ether (250 ml.) is added to a mixture of lithium aluminum hydride (3.42 g., 90 mM) and ether (250 ml.). Aluminum chloride (0.18 g., 1.35 mM) is added and the mixture refluxed for 12 hours and then cooled. Water (3.4 ml.), sodium hydroxide (3.4 ml. of 6 N) and water (10 ml.) are then added successively to the reaction mixture. The inorganic salts which precipitate are filtered off and the filtrate is then concentrated in vacuo to give the desired alcohol as an oil - 2.4 g. (98%).

Workup

  1. temperaturethe mixture refluxed for 12 hours
  2. temperaturecooled
  3. filtrationThe inorganic salts which precipitate are filtered off
  4. concentrationthe filtrate is then concentrated in vacuo

Sources & evidence

ORD record
ord-9f736949ea0f4327b64ecf3024c8f0a0
Source dataset
uspto-grants-1983_04
Patent number
US04380542

Reaction notes

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