Sulfuric Acid → HCID 54535409, compound

HRID 322252Notes

Reaction equation

HRID 322252 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([O:18][C:19]1[CH:31]=[CH:30][C:22]([CH:23]=[CH:24][C:25](OCC)=[O:26])=[CH:21][C:20]=1[O:32][CH3:33])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)O>C(OCC)C.O>[CH2:11]([O:18][C:19]1[CH:31]=[CH:30][C:22]([CH:23]=[CH:24][CH2:25][OH:26])=[CH:21][C:20]=1[O:32][CH3:33])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 4065946HCID 4065946, compoundHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 54535409HCID 54535409, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent4×

Procedure

A solution of aluminum chloride (7.07 g) in diethyl ether (90 ml) was added dropwise, at 0° C., to a suspension of lithium aluminum hydride (7.59 g) in diethyl ether (300 ml). The mixture was stirred for 15 minutes, to which was added dropwise, at 0° C., a solution of ethyl 4-benzyloxy-3-methoxycinnamate (50,0 g) in diethyl ether (250 ml). The mixture was stirred for one hour at room temperature, to which was added water (200 ml), then, was carefully added 5N sulfuric acid (280 ml) at 0° C. The diethyl ether layer was taken. The aqueous layer was extracted with ethyl acetate. Organic layers were combined, washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (3:2, v/v), 3-(4-benzyloxy-3-methoxyphenyl)-2-propen-1-ol (34.2 g, 79%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 81-82° C.

Workup

  1. additionwas added dropwise, at 0° C.
  2. stirringThe mixture was stirred for one hour at room temperature, to which
  3. customat 0° C
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. washFrom the fraction eluted with ethyl acetate-hexane (3:2

Sources & evidence

ORD record
ord-16cf240cf585483c995968a2cbb5a20b
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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