Water → 6-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid

HRID 2393187Notes

Reaction equation

C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[C:22]1(O)[CH:27]=CC=[CH:24][CH:23]=1.B(F)(F)F.C[CH2:34][O:35][CH2:36][CH3:37].[OH2:38]>ClCCl>[CH3:34][O:35][C:36]1[CH:37]=[CH:24][C:23]([CH:14]([C:4]2[C:3](=[O:2])[C:12]3[C:7]([C:6](=[O:38])[C:5]=2[CH3:13])=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:22][CH:27]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of 6-(1-methoxy-3-methylnaphth-2-yl)-5-hexenoic acid (70 g) and phenol (70 g) in dichloromethane (500 ml) was added boron trifluoride etherate (95 g) and the reaction mixture was stirred for 3 days at 35° C. and poured into cooled water. The organic layer was washed with water, dried, and evaporated. The residue was purified with silica gel chromatography (eluent; toluene, 20% ethyl acetate/hexane, and ethyl acetate) to give the titled compound (30 g).

Workup

additionpoured
washThe organic layer was washed with water
customdried
customevaporated
customThe residue was purified with silica gel chromatography (eluent; toluene, 20% ethyl acetate/hexane, and ethyl acetate)

Sources & evidence

ORD record: ord-1470db528db146f7b88e40d64e826c39
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05804601

Reaction notes

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