Hydrochloric Acid → HCID 21473911, compound

HRID 742313Notes

Reaction equation

HRID 742313 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH:6]([C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:10][CH:9]=1)=[O:7].Cl>C(OCC)C.O1CCCC1>[OH:7][CH:6]([C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:10][CH:9]=1)[CH2:3][CH:2]=[CH2:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2751588Tert-butyl 4-formylbenzoateHCID 178455850HCID 178455850, compound

Product 1

HCID 21473911HCID 21473911, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1.0M solution (200 ml, 200 ml) of allylmagnesium bromide in diethyl ether was dropped into a solution of t-butyl 4-formylbenzoate (30.9 g, 150 mmol) in anhydrous tetrahydrofuran, while stirring the latter under cooling with ice in a nitrogen stream. After the completion of the dropping, the obtained mixture was further stirred for 30 minutes, followed by the addition of 220 ml of 1N hydrochloric acid cooled with ice. The obtained mixture was vigorously stirred. The aqueous layer was further extracted with diethyl ether. The organic layers were combined, washed with an aqueous solution of common salt, dried and concentrated. The residue was purified by silica gel column chromatography to give t-butyl 4-(1-hydroxy-3-butenyl)benzoate. Yield: 8.2 g.

Workup

  1. temperatureunder cooling with ice in a nitrogen stream
  2. stirringAfter the completion of the dropping, the obtained mixture was further stirred for 30 minutes
  3. temperaturecooled with ice
  4. stirringThe obtained mixture was vigorously stirred
  5. extractionThe aqueous layer was further extracted with diethyl ether
  6. washwashed with an aqueous solution of common salt
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b47ce03db9cb4f4e91ee420a69d595e9
Source dataset
uspto-grants-1996_09
Patent number
US05554615

Reaction notes

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