Phenol → e-4-[4-(2-Benzyloxyethoxy)phenyl]-3,4-diphenyl-but-3-en-1-ol

HRID 1937656Notes

Reaction equation

HRID 1937656 reaction equation
C1(O)C=CC=CC=1.[CH2:8]([O:15][CH2:16][CH2:17]Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH:19][CH2:20][CH2:21]/[C:22](/[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[C:23](\[C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:8]([O:15][CH2:16][CH2:17][O:36][C:33]1[CH:32]=[CH:31][C:30](/[C:23](/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:22](/[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)\[CH2:21][CH2:20][OH:19])=[CH:35][CH:34]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 13298066HCID 13298066, compound

Product 1

HCID 22461338e-4-[4-(2-Benzyloxyethoxy)phenyl]-3,4-diphenyl-but-3-en-1-ol

Procedure

The alkylation of the starting phenol with benzyl-(2-bromoethyl)ether was carried out as described in Example 1 of the International Patent Application WO 96/07402 with the exception that now the starting compound was the other geometric isomer, E-4-(4-hydroxy-1,2-diphenyl-but-1-enyl)-phenol which was prepared by the method described in U.S. Pat. No. 4,996,225. The product was extracted to toluene. The toluene phases were combined, washed with water, dried and evaporated to dryness. The residue was recrystallized from a minor quantity of toluene and the precipitated product was used in the next step without further purification.

Workup

  1. customwas prepared by the method
  2. extractionThe product was extracted to toluene
  3. washwashed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was recrystallized from a minor quantity of toluene
  7. customthe precipitated product was used in the next step without further purification

Sources & evidence

ORD record
ord-2d438b6e82494ca1a1389d48de792f0d
Source dataset
uspto-grants-2002_05
Patent number
US06395785B1

Reaction notes

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