Methanol → HCID 54444943, compound

HRID 1939967Notes

Reaction equation

C(O[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]([O:18]CC)=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(Cl)Cl.[H-].C([Al+]CC(C)C)C(C)C.C[OH:42].[C:43]1([CH3:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O>[CH2:49]([O:42][C:11]1[CH:10]=[CH:9][CH:14]=[CH:13][C:12]=1[CH:15]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:16]=[O:18])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

Conditions

Temperature: -70 °C

Procedure

9.5 g (0.026 mol) of ethyl 2-(4-benzyloxyphenyl)-3-phenylpropionate, 40 ml of toluene and 30 ml of methylene chloride are introduced into a three-necked flask. The mixture is cooled to -70° C. 44 ml of 1M diisobutylaluminium hydride in toluene are added over a period of 15 minutes. The mixture is stirred at that temperature for one hour. 30 ml of methanol and 60 ml of water are added at -70° C. The alumina is filtered off and the aqueous phase is extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated to dryness. There are obtained 8.2 g of 2-benzyloxyphenyl-3-phenylpropionaldehyde. Yield: 100%.

Workup

filtrationThe alumina is filtered off
extractionthe aqueous phase is extracted with methylene chloride
dry with materialThe combined organic phases are dried over sodium sulphate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-e0bee36957484b76a15fe672c356b4e1
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698567

Reaction notes

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