Potassium Carbonate → 4-(2-Benzyloxyphenyl)-3-buten-1-ol

HRID 987259Notes

Reaction equation

HRID 987259 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[OH:18][CH2:19][CH2:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[CH:21][CH2:20][CH2:19][OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3447842-(Benzyloxy)benzaldehydeHCID 11025793(3-Hydroxypropyl)triphenylphosphonium bromide

Product 1

HCID 543076124-(2-Benzyloxyphenyl)-3-buten-1-olYield 89.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Benzyloxybenzaldehyde (8 g; 37 mmole), (3-hydroxypropyl)triphenylphosponium bromide (19.5 g; 47 mmole) and potassium carbonate (6.6 g; 48 mmole) were mixed in isopropanol. The reaction mixture was refluxed over night then filtered and the filtrate was evaporated. Chromatography using ethyl acetate:dichloromethane (up to 5%) as eluant gave 8.4 g (87.6%) of 4-(2-benzyloxyphenyl)-3-buten-1-ol. Both cis and trans 4-(2-benzyloxyphenyl)-3-buten-1-ol were formed according to NMR.

Workup

  1. temperatureThe reaction mixture was refluxed over night
  2. filtrationthen filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-efcedab9397d46f68cfce0f6f7c7c86e
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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