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Benzyl Bromide → 6-{2-[6-[(4-acetoxyphenyl)methoxy]-2,4-dichlorophenyl]ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

HRID 1285605
Notes
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Reaction equation

HRID 1285605 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([OH:9])[C:3]=1[CH2:10][CH2:11][CH:12]1[O:17][C:16](=[O:18])[CH2:15][CH:14]([OH:19])[CH2:13]1.[C:20]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1)(=[O:22])[CH3:21].ClC1C=C(O)C(=C(Cl)C=1)C=O.C(Br)C1C=CC=CC=1>>[C:20]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:9][C:4]2[C:3]([CH2:10][CH2:11][CH:12]3[O:17][C:16](=[O:18])[CH2:15][CH:14]([OH:19])[CH2:13]3)=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[CH:26][CH:25]=1)(=[O:22])[CH3:21]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 5283902,4-Dichloro-6-hydroxybenzaldehydeHCID 109987714-(Bromomethyl)phenyl acetateHCID 135531966-{2-(2,4-Dichloro-6-hydroxyphenyl)-ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

Product 1

HCID 201590376-{2-[6-[(4-acetoxyphenyl)methoxy]-2,4-dichlorophenyl]ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

Procedure

By following the procedure of Example 1, Step A, but substituting equimolar amounts of 6-[2-(2,4-dichloro-6-hydroxyphenyl)ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one and 4-(bromomethyl)phenol acetate for the 4,6-dichlorosalicylaldehyde and benzyl bromide used therein, the title compound is obtained.

Sources & evidence

ORD record
ord-be808a0915ed4596b83a8558eb23decf
Source dataset
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04567289

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes